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1,2,4-Triazole synthesis
Description
Base-catalyzed synthesis of substituted 1,2,4-triazoles can be performed by the condensation of a nitrile and a hydrazide.
References
Tetrahedron Letters, 2005, 46(19), 3429-3432.
2+2*1+1 Imidazole synthesis
Description
Synthesis of imidazoles from 1,2-diketones via cyclocondensation with ammonia and aldehydes to form imidazole derivatives.
References
Organic Letters, 2004, 6(9), 1453-1456.
2,3-Dihydro-1H-benzimidazole synthesis
Description
The acid-catalyzed condensation reactions of o-phenylenediamines with appropriate carbonyl compounds (aldehyde or ketone) afford dihydrobenzimidazoles.
References
Synthetic Communications, 1983, 13(12), 1033-1039.
3+2 Dihydroimidazole thione synthesis
Description
Condensation of alpha-aminocarbonyl compound with various isothiocyanates or a thiocyanate salt (i.e. KSCN) leads to the N-substituted cyclic thioureas through the acyclic thiourea intermediates.
References
Bioorganic & Medicinal Chemistry, 2005, 13(13), 4209-4220.
3+2 Furan synthesis
Description
This is a furan synthesis by 3+2 ring closure reaction. It can be assumed that the reaction proceeded through a preliminary Knoevenagel condensation between alpha-haloketone and beta-ketoester followed by condensation to provide furan derivatives.
References
Journal of the American Chemical Society, 1951, 73, 356-358.
3+2 Pyrazole synthesis
Description
Condensation of hydrazines/hydrazides and 1,3-dicarbonyl compounds with acid leads to pyrazoles or substituted pyrazoles. Hydrazines/hydrazides reacted efficiently with various beta-diketones to afford the desired pyrazoles in good to excellent yields. The reactions between hydrazines/hydrazides and symmetrical beta-diketones gave single components; when an unsymmetrical beta-diketone is employed to react with hydrazines or hydrazides, two regioisomers can be formed.
References
Bioorganic & Medicinal Chemistry Letters, 2009, 19(17), 4963-4966.
Acylation of amine
Description
Acylation of amines is an important method for protection of their basic functionality. Amines can react with a carboxylic acids or their derivatives and the reaction goes via tetrahedral intermediate. The acylating agents can be carboxylic acids, acid halides, esters, anhydrides, thiol acids and other acid derivatives.
References
No references
Acylation of nucleophiles with acid chlorides
Description
Nucleophilic acyl substitution of amines, alcohols and thiols with acyl chlorides.
References
Synthetic Communications, 2002, 32, 23–30.
Acylation of nucleophiles with carboxylic acids
Description
Nucleophilic acyl substitution of carboxylic acids with amines, alcohols or thiols to form amide, ester or thioester synthesis. The acid catalysed protonation provides extremly powerful electrophiles to form tetrahedral intermediate with nucleophiles. Carboxylic acid do not undergo substitution reaction under basic conditions, deprotonation of the acid gives the carboxylate salt.
References
No references
Addition of alcohols to alkynes
Description
The addition of alcohols to alkynes proceeds to give the corresponding enol ethers.
References
Catalytic Heterofunctionalization, Antonio Togni, Hansjorg Grutzmacher, 2001, pg.no: 204-205.
Tetrahedron, 2006, 62, 2231-2234.
Tetrahedron Letters 50 (2009) 570–573.
Addition of hydrogen cyanide to alkynes
Description
Addition of hydrogen cyanide to alkynes yields alkenyl cyanide.
References
Modern Organonickel Chemistry, Yoshinao Tamaru, 2005, pg.no: 111;
Principles of Organic Chemistry, Peter R. S. Murray, 1977, pg.no: 118.
J Chem Soc, Chemical Communications, 1982, 21, 1231-1232.
Aldol reaction
Description
The enolate of an aldehyde or a ketone reacts at the α-carbon with the carbonyl of another molecule aldehyde or ketone under basic or acidic conditions to obtain β-hydroxy aldehyde or ketone. Base-catalysed aldol reactions may give the aldol product, or may give the dehydrated enone or enal by an E1cB mechanism. Acid-catalysed aldol reactions may give the aldol product, but usually give the dehydrated enone or enal by an E1 mechanism. In the case of cross condensation (occur between two different carbonyl compounds) one partner only must be capable of enolization, the other partner must be incapable of enolization and be more electrophilic than the enolizable partner.
References
No references
Alkyl Lithium formation from alkyl halides
Description
Alkyl halide reacts with lithium metal to form alkyl lithium.
References
Organic chemistry, Marye Anne Fox, James K. Whitesell, 1997, pg. no.532;
Organic chemistry: an intermediate text, Robert V. Hoffman, 2004, pg. no.224;
Organolithiums: selectivity for synthesis, Jonathan Clayden, 2002, pg. no.152;
Invitation to organic chemistry, A William Johnson, 1999, pg. no.106.
Alkylation of amines with alkyl halides
Description
This reaction is a nucleophilic attack of alkyl halides by primary or secondary amines, which usually gives a mixture of secondary and tertiary amines. Aryl halides are much less reactive than alkyl halides in the nucleophilic substitution reactions.
References
No references
Alkylation of phenols with benzyl chloride
Description
Preparation of benzyl-phenyl ethers with benzyl chloride in the presence of potassium carbonate.
References
Resorcinol: chemistry, technology, and applications, Raj B. Durairaj, 2005, pg. no.48;
Comprehensive organic functional group transformations: synthesis: carbon, Alan R Katrizsky, Steven V.Ley, Otto Meth-Cohn, Charles W. Ress, FRS, 1995, pg. no.683;
Current medicinal chemistry, May 1994, pg. no.93;
Handbook of hydroxyacetophenones: preparation and physical properties, Volume 1, Robert Martin, 2005, pg. no.362.
Tetrahedron Letters, 2008, 49, 5039-5042.
Allylic halogenation of alkenes
Description
Alkenes undergo allylic halogenation via free radical mechanism.
References
Organic Chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 216, 217;
Organic Chemistry, Solomons & Fryhle, 2006, pg.no: 695;
Christopher J. Easton, Alison J. Edwards, Stephen B. McNabb, Martin C. Merrett, Jenny L. O'Connell, Gregory W. Simpson, Jamie S. Simpson and Anthony C. Willis, Org. Biomol. Chem., 2003, 1, 2492 - 2498.
Alpha halogenation of carboxylic acids
Description
Carbonyl compounds can be halogenated in the alpha position by halogens in acidic or basic solutions. The acid catalyzed enol formation is followed by the electrophilic attack of the halogen. In the case of the base catalysed reaction enolate is formed first followed by the halogenation, that usually won’t stop at the introduction of one halogen atom.
References
Synthetic Communication, 2004, 34, 889–893.
Arylation of amines
Description
This is a nucleophilic substitution (SNAr) reaction, which requires catalyst to initiate the reaction.
References
No references
Baylis-Hillman vinyl alkylation
Description
Amine catalyzed conversion of activated (electron-poor) alkenes to alpha-hydroxyalkyl olefines with carbonyl compounds.
References
Baylis, A.B., Hillman, M.E.D. Ger. Pat. 2155113, C.A., 1972, 77, 3417;
Baylis, A.B., Hillman, M.E.D, U.S. pat. 3743669 (1972, 1973);
Basavaiah D., Tetrahedron Lett., 1986, 27, 2031;
Basavaiah D., Tetrahedron Lett., 1987, 28, 4591, 4351;
Basavaiah D., Tetrahedron Lett., 1990, 31, 1621;
Drewes, S.E., Roos, G.H.P., Tetrahedron, 1988, 44, 4653;
Tetrahedron Lett., 2002, 43, 25, 4499;
K.-S. Park, J. Kim, H. Choo, Y. Chong, Synlett, 2007, Pg. no 395-398;
J. Cai, Z. Zhou, G. Zhao, C. Tang, Org. Lett., 2002, 4, 4723-4725;
H. Ito, Y. Takenaka, S. Fukunishi, K. Iguchi, Synthesis, 2005, 3035-3038;
C. Yu, L. Hu, J. Org. Chem., 2002, 67, 219-223;
K. Matsui, S. Takizawa, H. Sasai, Synlett, 2006, pg.no: 761-765.
Organic Letter, 2002, 4, 4723-4725.
Benzidine rearrangement
Description
Benzidine rearrangement is an acid-catalyzed intramolecular rearrangement of aromatic hydrazocompounds. The name of the rearrangement has been derived from the major product; benzidine (4, 4'- diaminodiphenyl hydrazine), which is formed when hydrazobenzene is warmed with dil HCl or H2SO4.
References
Organic Reactions, Rajpal Tyagi, 2005, Pg. no: 43;
Synthesis of biaryls, Ivica Cepanec, 2004, Pg. no: 275, 276;
A. Burawoy, C. E. Vellins Journal of the Chemical Society 1954, 90;
H. R. Snyder, C. Weaver, C. D. Marshall, Journal of the American Chemical Society 1949, 7l, 289;
M. Nojima, T. Ando, N. Tokura, Journal of the Chemical Society, Perkin Transaction I 1976, 14, 1504;
Name reactions and reagents In Organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, 2005, Pg. no: 85;
Organic Letters, 2006, 8, 2047-2050.
March's Advanved Organic Chmistry, 5th Edition, 2001: The Benzidine Rearrangement
Benzimidazole synthesis
Description
A traditional method for synthesis of benzimidazoles is the reaction between phenylenediamine and carboxylic acid under harsh dehydrating reaction conditions, for example, in the presence of HCl, polyphosphoric acid, H3BO3, or p-toluenesulfonic acid.
References
Organic Process Research & Development, 2010, 14(1), 215-224.
Benzothiazole synthesis
Description
The reaction of 2-aminothiophenol and aryl aldehyde providing 2-aryl benzothiazole derivatives. Aliphatic aldehydes show poor yields of the desired products. This condensation–oxidation procedure is fairly general, and several functionalities, including hydroxyl and conjugated carbon–carbon double bonds, are tolerated.
References
Synthetic Communications, 2010, 40, 206-212.
Benzoxazole synthesis
Description
The reaction of 2-aminothiophenol and aryl aldehyde providing 2-aryl benzothiazole derivatives. Aliphatic aldehydes show poor yields of the desired products. This condensation–oxidation procedure is fairly general, and several functionalities, including hydroxyl and conjugated carbon–carbon double bonds, are tolerated.
References
Angewandte Chemie, International Edition, 2008, 47, 9330-9333.
Beta HX elimination (Zaitsev elimination)
Description
Alkyl halides typically undergo beta elimination reaction when heated with strong bases, hydroxides and alkoxides, to generate alkenes. The reaction involves loss of H and a halogen atom from adjacent carbons. The major reaction product is the alkene with more highly substituted (more stable) double bond.
References
Organic reaction mechanisms, V. K. Ahluwalia, Rakesh Kumar Parashar, 2002, pg. no. 58;
Organic chemistry (Sie), Carey, 2008, pg. no. 205, 206, 207, 339.
J Org Chem, 1970, 35, 1335-1338;
J Org Chem 1982,47,1944-1948;
Acc Chem Res, 1975, 8, 239-245;
Acc Chem Res, 1979, 12, 198-203;
March's Advanced Organic Chemistry, 5th ed., 2001.
Birch reduction
Description
The reduction of aromatic compounds by alkali metals in liquid ammonia in the presence of an alcohol is called the Birch reduction, and yields selectively the 1,4-hydrogenated product.
References
Hydrocarbon chemistry, Arpad Molnar, 2003, Pg. no: 648.
Organic Reactions, Rajpal Tyagi, 2005, Pg. no: 71.
Synthetic approaches in organic chemistry, Raj K. Bansal, 1996, Pg. no: 114, 115,117;
Comprehensive Organic Synthesis, Barry M. Trost, Ian Fleming, 1992, Pg. no: 496.ű
Chem. Commun., 1999, 1263–1271
J Am Chem Soc, 1990, 112, 1280-1281
J Am Chem Soc, 1993, 115, 2205-2216
Bromination of aliphatic nitro compounds
Description
Primary and secondary nitro compounds on treatment with Br2 in alkaline medium undergo bromination at alpha position.
References
Patent number: US 2632776, Mar. 24, 1953;
Organic Chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no.759;
Patent number: US 5180859, Jan. 19, 1993
J Org Chem, 1977, 42, 3764-3765.
Carboxylic acid addition to alkynes (Markovnikov)
Description
Markovnikov addition of carboxylic acid to terminal alkyne produce enol ester.
References
Ruthenium in Organic Synthesis, Shun-Ichi Murahashi, 2004, pg.no: 197;
Immobilized catalysts: solid phases, immobilization and applications, Andreas Kirschning, 2004, page no. 125.
H. Doucet, B. Martin-Vaca, C. Bruneau, P.H. Dixneuf, J Org Chem, 60:7247-7255(1995);
L.J. Goossen, J. Paetzold, D. Koley, ChemComm, 706-707(2003);
J. Tripathy, M. Bhattacharjee, Tetrahedron Letters, 50:4863-4865(2009);
Tetrahedron Letters, 2002, 43, 9259-9263.
Carboxylic acid addition to alkynes (anti-Markovnikov)
Description
Anti-Markovnikov addition of carboxylic acid to alkyne yields enol ester.
References
Advanced Organic Chemistry,Francis A. Carey,2001, pg.no: 373;
P.E. Peterson and J.E. Dudley, J. Am. Chem. Soc, 88:4990 (1966);
R.H. Summearville, C.A. Senkler, P.V.R. Schleyer, J. Am. Chem. Soc, 96:1100 (1974);
Metal Vinylidenes and Allenylidenes in Catalysis, Christian Bruneau, Pierre Dixneuf, 2008, pg.no: 316;
Ruthenium Catalysts and Fine Chemistry, Christian Bruneau, Pierre H. Dixneuf, 2004, pg.no:130.
L.J. Goossen, J. Paetzold, D. Koley, Chem. Comm., 706-707(2003);
J. Tripathy, M. Bhattacharjee, Tetrahedron Letters, 50:4863-4865(2009);
H. Doucet, B. Martin-Vaca, C. Bruneau, P.H. Dixneuf, J. Org. Chem., 60:7247-7255(1995);
Catalytic hydration of alkenes
Description
Alkenes undergo catalytic hydration to form carbonyl compounds.
References
Transition metal reagents and catalysts, Jiro Tsuji, 2002, pg.no: 421, 422;
Advanced Organic Chemistry: Part B: Reactions and Synthesis, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 710, 711.
Organic Synthesis, 1990, 7, 137.
Catalytic hydrogenation of aromatic compounds with Rh_C or Pt_C
Description
Catalytic hydrogenation of aromatic compounds in presence of catalytic amounts of Rh/C or Pt/C to form hydrogenated cyclic compounds.
References
Heterogeneous catalysis for the synthetic chemist, Robert L. Augustine, 1996, pg. no.408, 416;
Green chemistry and catalysis, Roger A. Sheldon, Isabel Arends, Ulf Hanefeld, 2007, pg. no.98;
Introduction to organic chemistry II, Seth Robert Elsheimer, 2000, pg. no.12;
Hydrocarbon chemistry, George Andrew Olah, Arpad Molnar, 1995, pg. no.632;
Comprehensive organic synthesis: selectivity, strategy, and efficiency, Barry M. Trost, Ian Fleming, 1991, pg. no.438.
Journal of Organometallic Chemistry, 2004, 689, 639–646.
Angew. Chem. Int. Ed., 2007, 46, 1152 –1155.
Catalytic hydrogenation of aromatic hydrocarbons with H2/Ni or H2/Pd-C
Description
Catalytic hydrogenation of aromatic hydrocarbons to alicylic compounds.
References
University Chemistry, Vol. I By C. Parameshwara Murthy, 2008, Page. no:408;
Aromatic chemistry, John D. Hepworth, David R. Waring, Michael J. Waring, 2002, Pg. no: 129;
Modern organonickel chemistry, Yoshinao Tamaru, 2005, Pg. no: 279;
Patent, EP2141167A1, 2010.
Some modern methods of organic synthesis By W. Carruthers, Edition:2 -1971, Page No. 310;
Comprehensive organic synthesis: selectivity, strategy & Efficiency in Modern Organic chemistry, Vol 8, Barry M. Trost, Ian Fleming, 1991, Pg. no: 438;
Heterogeneous catalysis for the synthetic chemist, Robert L. Augustine, 1996, Pg. no: 403 & 418.
Catalytic hydrogenation of phenols
Description
Selective hydrogenation of phenol to cyclohexanones takes place under a variety of conditions and over different catalysts.
References
1. Industrial organic chemicals, Part 2, Harold Wittcoff, B. G. Reuben, Jeffrey S. Plotkin, 2004, pg. no.283;
2. High pressure chemistry: synthetic, mechanistic, and supercritical applications, Rudi Van Eldik, Frank-Gerrit Klarner, 2002, pg. no.386;
3. Some modern methods of organic synthesis, W. Carruthers, 2004, pg. no.419;
4. Heterogeneous catalysis for the synthetic chemist, Robert L. Augustine, 1996, pg. no.412.
5. US patent 3965187
Chan reduction of acetylenes
Description
Stereoselective reduction of propargyl alcohols to E-allylic alcohols by means of sodium bis(2-methoxyethoxy)aluminium hydride (SMEAH or Red-Al) or LiAlH4.
References
Ka-Kong Chan, J. Org. Chem. 1976, 41, 62;
Ka-Kong Chan, N. Cohen, J.P. De Noble, A.C. Specian, Jr. G. Saucy, J. Org. Chem. 1976, 41, 3497;
Ka-Kong Chan, J. Org. Chem. 1978, 43, 3435;
N.M. Irvine, Phytochemistry, 2000, 53, 349-355;
E.J. Corey, J.A. Katzenellenboger, G.H. Posner, J. Am.Chem. Soc. 1967, 89, 4245-4247;
S.E. Denmark, T.K. Jones, J. Org. Chem. 1982, 47, 4595-4597;
J.A. Marshall, B.S. DeHoff, J. Org. Chem. 1986, 51, 863-872;
D.J. Kucera, S.J. O'Connor, L.E. Overman, J. Org. Chem. 1993, 58, 5304-5306;
E. Roulland, C. Monneret, J.-C. Florent, J. Org. Chem. 2002, 67, 4399-4406;
C.T. Meta, K. Koide, Org. Lett. 2004, 11, 6, 1785-1787;
Organic synthesis based on name reactions, A. Hassner and C.stumper, 2002, pg.no: 56;
Name reactions by Jie Jack Li, 2006, pg.no: 114;
Midland, M. M. Gabriel, J. J. Org. Chem. 1985, 50, 1143;
Meta. C.T. Koide, K. Org. Lett.2004, 6, 1785;
Name reactions and reagents in Organic synthesis, 2nd Edition, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, Jr., pg.no: 139;
E. B. Bates, E. R. H. Jones, M. C. Whiting, Journal of the Chemical Society, 1954, 1854;
T. Eguchi, T. Koudate, K. Kakinuma, Tetrahedron, 1993,49,4527;
C. Agami, M. Cases, F. Couty, Journal of Organic Chemistry, 1994,59,1931.
Organic Letters, 2004, 6, 4073-4076.
Journal of Organic Chemistry, 1995, 60, 6046-6056.
Cleavage of acyclic ethers with HI (SN1 mechanism)
Description
Tertiary ethers undergoes cleavage with HI by an SN1 mechanism to form an alcohol and an alkyliodide. Cleavage of the C-O bond then occurs in two steps, the bond to the leaving group is broken to form a carbocation, and then the bond to the nucleophile is formed. This generates alkyl iodide.
References
Organic chemistry (Sie) 2E, 2008, pg. no.345;
Chem 4113 Organic chemistry II, Lecture notes, chapter 18.
J. Org. Chem. 2000, 65, 7740-7746.
Cleavage of acyclic ethers with HI (SN1 mechanism)
Description
Tertiary ethers undergoes cleavage with HI by an SN1 mechanism to form an alcohol and an alkyliodide. Cleavage of the C-O bond then occurs in two steps, the bond to the leaving group is broken to form a carbocation, and then the bond to the nucleophile is formed. This generates alkyl iodide.
References
Organic chemistry (Sie) 2E, 2008, pg. no.345;
Chem 4113 Organic chemistry II, Lecture notes, chapter 18.
J. Org. Chem. 2000, 65, 7740-7746.
Cleavage of epoxides
Description
Hydrolysis of epoxides leading to diols via carbocation rearrangement (mechanism analogous to SN1 and SN2 operate under neutral and acid catalyzed conditions).
References
Synthesis, 17, 2005, 2897-2900;
J. Org. Chem., 2008, 73, 2270-2274;
Advanced organic chemistry: structure and mechanisms, Francis A. Carey, Richard J. Sundberg, 2001, pg. no.513;
Catalytic oxidations with hydrogen peroxide as oxidant, Giorgio Strukul, 1992, pg. no.28.
Cleavage of ethers with HI (SN2 mechanism)
Description
Primary and secondary ethers are cleaved by strong acids such as hydroiodic acid (or HBr) in a nucleophilic substitution (SN2) reaction to form an alcohol and an alkyliodide.
References
The Last American Frontier, Frederic L. Paxson, 2001, pg. no.299;
Organic Chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, pg. no. 427;
Organic Chemistry: Aromatic, Alcohols Aldehydes & Acids, Amit Arora, pg. no. 103;
Organic Chemistry, J. William Suggs, pg. no. 255;
Organic chemistry, Dhawan, 2007, pg. no.7-9.
J. Org. Chem. 2000, 65, 7740-7746.
Cleavage of vinyl ethers
Description
Acid-catalyzed cleavage of the vinyl ethers to give alcohols and carbonyl compounds (aldehyde or ketone).
References
Hydrolysis of vinyl ethers, US Patent 2533172, 1950;
Organic chemistry, Thomas N. Sorrell, 2006, pg.no.638;
Can. J. Chem. Vol. 65. 1987
Journal of Organometallic Chemistry 692 (2007) 472–480;
Clemmensen reduction
Description
Clemmensen reaction is a reduction of carbonyl functional group of aldehydes or ketones. It employs zinc metal dissolving in concentrated hydrochloric acid; this reaction is really reasonable only for compounds with just the one functional group. The Clemmensen reduction is complementary to the Wolff-Kishner reduction, which is run under strongly basic conditions. Acid-labile molecules should be reduced by the Wolff-Kishner protocol.
References
No references
Condensation reaction of primary amines and oxocompounds
Description
Nucleophilic addition-elimination reaction, addition of ammonia or primary amines type RNH2 or ArNH2 to aldehydes and ketones results in carbinolamine which undergoes dehydration to form the corresponding imine and a molecule of water. (A number of compounds of the general type H2NZ react with aldehydes and ketones in a manner analogous to that of primary amines).
References
No references
Condensation reaction of secondary amines and oxocompounds
Description
In the first step nucleophilic attack of amine to the carbonyl group results in carbinolamine which undergoes dehydration to yield an alkenyl-substituted amine, or enamine and a molecule of water. In general, ketones react more slowly and longer reaction times are often required. Enamine and imine are tautomers, enamines are normally stable when there is no hydrogen on the nitrogen.
References
No references
Corey-Chaykovsky reaction
Description
Corey-Chaykovsky reaction entails the reaction of sulfur ylide, either dimethylsulfoxonium methylide (Corey's ylide, sometimes known as DMSY) or dimethylsulfonium methylide, with electrophile, such as carbonyl, olefin, imine, or tiocarbonyl, to offer the corresponding epoxide, cyclopropane, aziridine, or thiirane.
References
Corey, E.J., J. Am. Chem. Coc., 1962, 84, 866;
Kuhn, R., Angew. Chem., 1957, 68, 570;
Kuhn, R., Liebigs Ann., 1958, 611, 117;
Olah, G.A., Synthesis, 1990, 887;
Name Reactions in Heterocyclic Chemistry, Jie Jack Li, 2004, pg.no: 2;
Name Reactions, Jie Jack Li, 2006, pg.no: 157,158;
R. J. Paxton, R. J. K. Taylor, Synlett, 2007, 633-637;
S. Chandrasekhar, Ch. Narasihmulu, V. Jagadeshwar, K. Venkatram Reddy, Tetrahedron Lett., 2003, 44, 3629-3630.
J. AM. CHEM. SOC. 2008, 130, 10078–10079
Dehalogenation of vicinal dihalides
Description
Elimination of dihalogens from vicinal dihalides resulting in the formation of olefins.
References
Organic Chemistry By Marye Anne Fox, James K. Whitesell, pg. no. 443;
Organic Chemistry (Sie), Pine, pg. no. 488, 489;
A textbook of organic chemistry, August Bernthsen, Raj K. Bansal, 2003, pg. no. 183;
Comprehensive Chemistry XI, pg. no. 1112.
Journal of Organic Chemistry, 2005, 70, 8621-8624.
Tetrahedron, 1998, 54, 1021-1028.
Reduction in organic chemistry, M. Hudlicky 1984 (Wiley-New York).
Dehydration of alcohols to alkenes
Description
Heating an alcohol with a catalytic amount of a strong acid (usually sulfuric acid or phosphoric acid) results in the formation of an alkene, with water as a byproduct. These dehydration reactions typically follow E1 mechanism.
References
Introduction to general, organic, and biochemistry, Frederick A. Bettelheim, William H. Brown, Mary K. Campbell,2009, pg. no. 379;
Organic Chemistry (sie), Carey, 2008, pg. no.197, 198, 199, 202;
General, Organic, and Biological chemistry, Stephen Stocker, 2009, pg. no.377;
Organic chemistry, Dhawan, 2007, pg. no. 6.25.
J. Org. Chem. 1980, 45, 919-920;
J. Org. Chem. 1967, 32, 3386-3389;
J. Org. Chem. 1982,47, 900-902;
Diazotisation of primary anilines
Description
Diazonium salt formation is a nitrosation reaction of primary aniline with nitrous acid which is formed in situ from sodium nitrite and strong acid such as HCl, H2SO4. In aqueous solution diazonium salts are unstable at temperatures above +5 °C. Aryl diazonium salts generally react with nucleophiles with loss of nitrogen. They are important intermediates in the formation of aryl halides (Sandmeyer and Schiemann reactions) and azo compounds.
References
No references
Diels-Alder cycloaddition
Description
4+2 cyclic addition of dienophile and diene to form an adduct.
References
Synthetic Approaches in Organic Chemistry, Raj K. Bansal, 1998, pg.no: 311, 312;
O.Diels and K. Alder, Ann., 460, 98 (1928);
J.Sauer, Angew. Chem.Int. Ed. (Engl), 6, 16 (1967);
The Diels-Alder reaction, Francesco Fringuelli, Aldo Taticchi, 2002, pg.no: 29, 30, 32, 35, 46, 51.
Organic Letters, 2005, 7, 2539-2541.
AngewChem-2008-47-6634.
Diels-Alder reaction with fused aromatic hydrocarbons
Description
Bachmann and Scott, J. Am. Chem. Soc, 1948, 70, 1458-61; Organic Reactions, Vol-IV, The Diels-Alder Reaction with Maleic Anhydride, Milton C Kloetzel, 1948, Pg. no: 11.
References
Chemistry under extreme or non-classical conditions, Rudi van Eldik, Colin D. Hubbard, 1996, Pg. no: 171;
Diels-Alder reaction between naphthalene and N-phenylmaleimide under ambient and high pressure conditions, Gulnara G. Iskhakova, Vladimir D. Kiselev, Elena A. Kashaeva, Lubov’ N. Potapova, Evgeny A. Berdnikov, Dmitry B. Krivolapov, and Igor A. Litvinov, 2005, Pg. no: 7;
Bachmann and Scott, J. Am. Chem. Soc, 1948, 70, 1458-61;
Organic Reactions, Vol-IV, The Diels-Alder Reaction with Maleic Anhydride, Milton C Kloetzel, 1948, Pg. no: 11, 30;
The Diels-Alder reaction, Francesco Fringuelli, Aldo Taticchi, 2002 , Pg. no: 196;
The Porphyrin Handbook, Volumes 11-20, Karl M. Kadish, Roger Guilard, Kevin M. Smith, 2003, Pg. no: 24;
Advanced Organic Chemistry, Francis A. Carey, Richard J. Sundberg, 2000, Pg. no: 859.
Org Lett, 2007, 7, 2859-2862.
Direct alkylation of amines with epoxide
Description
This is a nucleophilic ring-opening reaction of epoxides by ammonia or amines.
References
No references
Doering-LaFlamme allene synthesis
Description
Allene synthesis from alkenes via geminal dihalocyclopropanes. (two-step reaction)
References
W. v. Doering, A.K. Hoffmann, J. Am. Chem. Soc., 1954, 76, 6162;
P.M. La Flamme, Tetrahedron, 1958, 2, 75;
W.R. Moore, H.R. Ward, J. Org. Chem., 1960, 25, 2073;
W.R. Moore, J. Org. Chem., 1962, 27, 4182;
L. Skattebol, Tetrahedron Lett. 1961, 167;
E. Chinoporos, Chem. Rev., 1963, 63, 235;
T. Kitayama, T. Masuda, K. Sakai, C. Imada, Y. Yonekura, Y. Kawai, Tetrahedron, 2006, 62, 47, 10859-10864;
V. Franzen, Reaktionsmechanismen I (Heidelberg, 1958), p 14;
T. J. Logan, Tetrahedron Lett., 1961, 2, 173;
L. Skettebol, Acta Chem.Scand., 1963, 17,1683;
L.K. Sydnes, Chem. Rev., 2003, 103, 1133-1150;
J. Hine, Divalent Carbon (New York, 1964), p 20;
M. Murray, Houben-Weyl 1977, 5/2a, 985;
V. Nair, Comp. Org. Syn. 1991, 4, 1009-1012;
US 2933544 (1960);
Organic syntheses based on name reactions, Alfred Hassner, C. Stumer, pg.no: 91.
Ether formation from alcohols
Description
Heating alcohol with concentrated sulfuric acid results in condensation of two molecules of alcohol with elimination of water molecule to form ether. The reaction is catalyzed by H+ ions to form oxonium ion that undergoes substitution (SN1 or SN2) by another molecule of alcohol to form ether.
References
Organic Chemistry (Sie), Carey, 2008, pg. no. 669;
The organic chemistry problem solver, Volume 2, Max Fogiel, Research and Education Association, 1994, pg. no. 588;
Organic chemistry demystified, D. R. Bloch, 2006, pg. no. 320;
Phenolic compound biochemistry, Wilfred Vermerris, Ralph Nicholson, 2006, pg. no. 47;
Comprehensive organic reactions in aqueous media, Chao-Jun Li, Tak-Hang Chan, 2007, pg. no. 135.
General, organic, and biological chemistry, H. Stephen Stoker, 2007, pg. no.378.
J. Org. Chem. 1996, 61, 324-328.
J. Am. Chem. Soc. 1999, 121, 10711-10718.
Fischer esterification
Description
When carboxylic acids are treated with large excess of an alcohol in the presence of strong acid catalyst, esters are formed. The reaction is an equilibrium process but can be driven to favor the ester by removing the water that is formed. The most commonly used acid catalysts are Lewis acids, sulfuric acid, tosic acid; for sensitive substrate dicyclohexylcarbodiimide is often used.
References
No references
Formation of acetals and ketals
Description
Acetals and ketals are formed by treatment of aldehydes and ketones with alcohols in the presence of acid catalysts. Lewis acids can be used in conjunction with alcohols. Acetals and ketals are quite stable to bases, therefore a useful method of protection of aldehyde or ketone functions from attack by bases.
References
No references
Formation of alkylated, alpha unsaturated nitro compound
Description
A base catalyzed C-C bond forming reaction between nitro compound and aldehyde; further elimination of water to produce alkylated alpha unsaturated nitro compound (nitroalkene). It is a two step reaction which involves the following steps. 1. Nitroaldol reaction: Condensation reaction between a nitro compound and aldehyde. 2. Dehydration: By suitable functionalization of the hydroxy group followed by a base-induced elimination of water from the resulting derivative.
References
Org. Lett., 2008, 10, 1449-1451;
The nitro group in organic synthesis, Noboru Ono, 2001, pg. no. 41, 166.
Formation of cyclic acetals and ketals
Description
The expected product of nucleophilic addition of the alcohol to the carbonyl group of aldehydes or ketones is called cyclic acetals or ketals. Cyclic acetals and ketals are often used to protect aldehydes and ketones, because acetals can be introduced and removed readily. The five- or six-membered 1,3-dioxanes and 1,3-dioxolans derived from ethylene glycol are the most commonly encountered examples.
References
No references
Friedel-Crafts acylation
Description
Acylation of aromatic compounds by means of acyl halides in the presence of Lewis acids.
References
No references
Friedel-Crafts alkylation
Description
The synthesis of an alkylated aromatic compound by reaction of an aromatic substrate with an alkyl halide, catalyzed by a Lewis acid, is called the Friedel–Crafts alkylation. The general principle is the intermediate formation of a carbenium ion species, which is capable of reacting as the electrophile in an electrophilic aromatic substitution reaction.
References
Hydrocarbon chemistry, Arpad Molnar, 2003, Pg. no: 229, 237, 233;
Instant notes organic chemistry, Graham L. Patrick, 2004, Pg. no: 142;
Advanced organic chemistry, Part 2, Francis A. Carey, Richard J. Sundberg, 2007, Pg. no: 1016;
Advanced organic chemistry, Francis A. Carey, Richard J. Sundberg, 2007, Pg. no: 583.
Organic Synthesis, 1943, 2, p. 243.
Fritsch-Buttenberg-Wiechell acetylene synthesis (rearrangement)
Description
Alpha elimination from haloethylenes leading via carbene rearrangement to acetylenes.
References
Fritsch, P.Liebigs Ann, 1894, 279, 319;
Buttenberg, W.P.Liebigs Ann, 1894, 279, 327;
Wiechell, H.Liebigs Ann, 1894, 279, 332;
Acetylene Chemistry, François Diederich, Peter J. Stang, Rik R. Tykwinski, pg.no.262;
Curtin, D.Y.J. Am. Chem. Soc., 1958, 80, 4599;
Kobrich, G.Chem. Ber, 1972, 105, 1674;
Kobrich, G.Angew. Chem. Int. Ed., 1965, 449;
Bothner-ByJ. Am. Chem. Soc., 1955, 77, 3293;
Pritchard, Bothner-By J. Phys. Chem., 1960, 64, 1271;
Simonetta, Carra Tetrahedron, 1963, 19(2), 467;
Thippeswamy Dissertation Abstr., 1964, 24(12), 5012;
Stang, P.J. Chem. Rev., 1978, 78, 383;
Satoh, T., Hayashi, Y., Yamakawa, K.Bull. Chem. Soc. Jpn., 1993, 66, 1866;
Kobrich, G.Angew. Chem. Int. Ed., 1972, 11, 473;
Stang, P. J., Fox, D. P.J. Org. Chem., 1978, 43, 364;
Mouries, V., et al.Synthesis, 1998, 271;
Creton, I. et al.Tetrahedron Lett., 1999, 40, 1899;
Kawase, T., et al., Chem. Letters, 1995, 499;
Rezaei, H., et al., Org. Letters, 2000, 2, 419;
Organic Syntheses Based on Name Reactions, Alfred Hassner, C. Stumer, pg.no:114;
Acetylene Chemistry, François Diederich, Peter J. Stang, Rik R. Tykwinski, pg.no: 262, 263, 270;
Aliphatic, alicyclic and saturated heterocyclic chemistry, William Parker, Chemical, pg.no: 58.
Grignard compound addition to carbonyl compounds
Description
Grignard reaction is the addition of an organomagnesium halide (Grignard reagent) to a ketone or aldehyde, to form a tertiary or secondary alcohol. The reaction with formaldehyde leads to a primary alcohol.
References
No references
Grignard reaction to carbonyl compounds
Description
Synthesis of primer, sec. or tert. alcohols via addition of Grignard reagent to carbonyl compounds.
References
Grignard, V.Compt. Rend., 1900, 130, 1322;
Eicher, Patai, "The Chemistry of the Carbonyl Group" Interscience Publishers, New York, 1966, pp. 621-693;
Kharash, Reinmuth, "Grignard Reactions of Nonmetallic Substances" Prentice-Hall Inc., Engelwood Cliffs, N.J., 1954, pp. 138-528;
Shirley, D.A., Org. React., 1954, 8, 28-58
Campbell, J.E., Englund, E.E., Burke, S.D., Org. Lett, 2002, 4(13), 2273;
Lai, Y.H., Synthesis, 1981, 585-604;
Huryn, D.M., Comp., Org. Syn., 1991, 1, 49;
Silverman, G.,Rakita, P. E., Kirk-Othmer Encyclopedia of Chemical Technology vol. 12 (Wiley-Interscience, New York, 4th ed., 1994), pp. 768-786;
Advanced Organic Chemistry, Reinhard Bruckner, 2002, pg.no: 331;
Invitation to Organic Chemistry, A. William Johnson, 1998, pg.no: 474;
Principles of Organic Synthesis, Richard O. C. Norman, Raymond Bonnett, James M. Coxon, 1993, pg.no: 193;
Organic chemistry, Thomas N. Sorrell, 2006, pg.no: 493;
Advanced organic chemistry, Francis A. Cary, Richard J. Sundberg, 2007, pg.no: 639;
The organic chemistry of sugars, Daniel E. Levy, Péter Fügedi, 2006, pg.no: 251.
J Am Chem Soc, 1963, 48, 348-355.
Grignard reagent formation
Description
Synthesis of Grignard reagent from alkyl or aryl halides.
References
No references
Halogen addition to alkenes
Description
Halogens react with alkenes by electrophilic addition to form vicinal dihalide.
References
Advanced Organic Chemistry, A. Carey, Richard J. Sundberg, 2000, pg.no: 200, 202;
Hydrocarbon Chemistry, A. Olah, Árpád Molnár, 2003, pg.no: 308;
J. H. Rolston and K. Yates. J. Am. Chem. Soc. 91:1469, (1969);
Organic Chemistry (Sie), 7th Ed, Francis A Carey, pg.no: 251;
R. O. C. Norman and C. B. Thomas, J. Chem, Soc. B 1967:598;
Advanced Organic Chemistry: Reactions and synthesis, Francis A. Carey, Richard J. Sundberg, Edition: 5, 2007, pg no: 303.
JOrgChem-1991-56-3073-3079.
OrgLett-2003-5-4501-4504.
Halogen addition to alkynes
Description
Addition of one equivalent of halogen to alkyne results in formation of dihaloalkenes.
References
Chemistry Vol (1 & 2), AK Srivastava and PC Jain, pg.no: 1304;
Organic Chemistry, J. William Suggs, 2002, pg.no: 181;
Advanced Organic Chemistry, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 540.
Tetrahedron, 2001, 57, 7417-7422.
Organic Letters, 2001, 3, 1061-1063.
J Am Chem Soc, 1938, 60, 1711-1713.
Halogenation of alcohols with hydrogen halides
Description
Nucleophilic substitution reaction of alcohols with hydrogen halides to generate an alkyl halide and water.
References
Principles of organic chemistry, By Peter R. S. Murray, 1977, pg. no.174;
Introduction to organic laboratory techniques: a small scale approach By Donald L. Pavia, 2005, pg. no.188;
Organic Chemistry (Sie), Carey, 2008, pg. no.148, 345.
Halogenation of alkanes (UV light)
Description
No description
References
Organic Chemistry, Robert Thornton Morrison, Robert Neilson Boyd, 2000, pg.no: 105, 448;
Unified Course in Chemistry, O.P.Agarwal, 2004-2005, pg.no: 492.
J. Org. Chem. 1997, 62, 236-237.
Eur. J. Org. Chem. 2006, 483–488
Halogenation of alkanes (substitution)
Description
Substitution reaction of alkane to produce alkyl halide.
References
P. Kovacic, H.C. Volz, J. Am. Chem. Soc., 1959, 81, 3261;
N.C. Deno, E.J. Gladfelter, D.G. Pohl, J. Org. Chem., 1979, 44, 21, 3728;
K.R. Brower, J. Org. Chem., 1987, 52, 798;
S. Rozen, C. Gal, J. Org. Chem., 1987, 52, 4928;
G. A. Olah, A. Wu, O. Farooq, J. Org. Chem., 1989, 54, 1463;
C.A. Wight, P.M. Kligmann, T.D. Botcher, A.J. Sedlacek, J. Phys. Chem., 1990, 94, 2487;
I. Akhrem, A. Orlinkov, S. Vitt, A. Chistyakov, Tetrahedr. Lett., 2002, 43, 1333;
R. Montoro, T. Wirth, Org. Lett., 2003, 5, 24, 4729;
D.P.Wayman, J.Y.C.Wang, W.R. Freeman, J. Org. Chem, 1963, 28, 3173;
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I. Akhrem, A. Orlinkov, S. Vitt, A. Chistyakov, Tetrahedr. Lett., 2002, 43, 1333;
R. Montoro, T. Wirth, Org. Lett., 2003, 5, 24, 4729.
Halogenation of aromatic hydrocarbons
Description
Halogenation of aromatic hydrocarbons takes place through electrophilic substitution to produce aryl halides.
References
Organic chemistry, Thomas N. Sorrell, 2006, Pg. no: 571;
Chemical Engineering Handbook, Research and Education Association Staff, James R. Ogden, James R. Ogden Research & Education Association Susa, 1999, Pg. no: B67;
Organic Chemistry, Bhupinder Mehta, 2005, Pg. no: 834;
Organic Chemistry, Bhupinder Mehta, 2005, Pg. no: 837;
The organic chemistry problem solver, Max Fogiel, Pg. no: 339;
Organic chemistry, Thomas N. Sorrell, 2006, Pg. no: 576;
Advanced Organic Chemistry, Francis A. Carey, Richard J. Sundberg, 2007, Pg. no: 701;
The organic chemistry problem solver, Max Fogiel, Pg. no: 338.
Tetrahedron Letters, 2010, 51, 340–342.
Hantzsch pyrrole synthesis
Description
The Hantzsch pyrrole synthesis is an alkylation-cyclocondensation reaction involving a primary amine, a beta-ketoester or beta-ketoamide and an alpha-haloketone or aldehyde leading to tetra- or pentasubstituted pyrroles. The reaction can be performed either as a three component reaction or in a two component pathway by first treating a primary amine with a beta-ketoester or beta-ketoamide to obtain an enaminone followed by reaction with an alpha-bromoketone to afford the pyrrole ring.
References
Bioorganic and Medical Chemistry Letters, 1998, 8, 2381-2384.
Hantzsch thiazole synthesis
Description
The cyclocondensation of alpha-halocarbonyl compounds with thioamides (Hantzsch synthesis) provide thiazoles. The Hantzsch synthesis involves three intermediate steps: the halogen atom of the alpha-halo aldehyde or alpha-halo ketone is nucleophilically substituted; the resulting S-alkyliminium salt undergoes a proton transfer; cyclization produces a salt which is converted into a 2,5-disubstituted thiazole in protic solvents by an acid-catalysed elimination of water. Thiazoles do not react as 1,3-dienes, i.e. they do not undergo a Diels-Alder reaction.
References
Tetrahedron, 2008, 64, 4384-4386.
Heck reaction (intermolecular)
Description
The Heck reaction is a palladium catalyzed C-C coupling between aryl or vinyl halides or pseudohalides (eg. triflates, tosylates, thiomethyls) and activated alkenes in the presence of base. One of the benefits of the Heck reaction is its outstanding trans selectivity.
References
R.F. Heck, J.P. Nolley Jr., J. Am. Chem. Soc., 1968, 90, 5518;
R.F. Heck, Acc. Chem. Res., 1979, 12, 146 (Review);
R.F. Heck, Org. React., 1982, 27, 345 (Review);
R.F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, London, 1985 (Review);
Y. Akita, A. Inoue, Y. Mori, A. Otha, Heterocycles, 1986, 24, 2093;
L.S. Hegedus, Transition Metals in the Synthesis of Complex Organic Molecule, 1994, University Science Books: Mill Valley, CA, pp 103-113 (Review);
I.P. Beletskaya, A.V. Cheprakov, Chem. Rev., 2000, 100, 3009 (Review);
C. Amatore, A. Jutand, Acc. Chem. Res., 2000, 33, 314 (Review);
R. Franzen, Can. J. Chem., 2000, 78, 957;
A. Mayasundari, D.G.J. Young, Tetrahedron Lett., 2001, 42, 203;
A. Haeberli, C. Leumann, J. Org. Lett., 2001, 3, 489;
W.-J. Liu, Y.-X. Xie, Y. Liang, J.-H. Li, Synthesis, 2006, 860-864;
J.H. Kirchoff, M.R. Netherton, I.D. Hill, G.C. Fu, J. Am. Chem. Soc., 2002, 124, 13662-13663;
K.L. Billingsley, K.W. Anderson, S.L. Buchwald, Angew. Chem. Int. Ed., 2006, 45, 3484-3488;
M.J. Martinelli, P.J. Reider, Org. Lett., 2006, 8, 1787-1789;
J. Baxter, D. Steinhuebel, M. Palucki, I.W. Davies, Org. Lett., 2005, 7, 215-218;
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M. Shimizu, C. Nakamaki, K. Shimono, M. Shelper, T. Kurahashi, T. Hiyama, J. Am. Chem. Soc., 2005, 127, 12506-12507;
G.A. Molander, C.R. Bernardi, J. Org. Chem., 2002, 67, 8424-8429;
B. Karimi, D. Enders, Org. Lett., 2006, 8, 1237-1240;
X. Cui, J. Li, Z.-P. Zhang, Y. Fu, L. Liu, Q.-X. Guo, J. Org. Chem., 2007, 72, 9342-9345;
H. J. Li, L. Wang, Eur. J. Org. Chem., 2006, 5101-5102;
A.-E. Wang, J.-H. Xie, L.-X. Wang, Q.-L. Zhou, Tetrahedron, 2005, 61, 259-266;
Paul De Mayo, Leiv K. Sydnes, Grazyna Wenska, J. Org. Chem., 1980, 45 (9), pp 1549–1556;
Geoffrey T. Crisp* and Markus G. Gebauer, Tetrahedron, 52, 1996, pg.no: 12465-12474;
Advanced Organic Chemistry: Reactions and synthesis, Francis A. Carey, Richard J. Sundberg, 2000, pg.no: 506;
Stereoselective Synthesis, Atta-ur- Rahman, 1988, pg.no: 427, 428;
Practical Microwave Synthesis for Organic Chemists, C. Oliver Kappe, Doris Dallinger, Shaun Murphree, 2009, pg.no: 216;
Name reactions for Homologation, By Jie Jack Li, E. J. Corey, 2009, Pg. No.21.
Heck reaction (intramolecular)
Description
Unhindered alkenes undergo intramolecular Heck reaction and forms C-C coupled compounds.
References
Transition Metal Reagents and Catalysts, Jiro Tsuji, 2002, pg.no: 45;
Palladium in heterocyclic chemistry, Jie Jack Li, Gordon W. Gribble,2000, pg.no: 56, 57;
Transition Metal Reagents and Catalysts, Jiro Tsuji, 2002, pg.no: 41,43;
Microwaves in Organic and Medicinal Chemistry, C. Oliver Kappe, Alexander Stadler, 2005, pg.no: 113.
J Am Chem Soc, 1996, 118, 12, 2843-2859.
Hinsberg thiophene synthesis
Description
Hinsberg synthesis is a condensation reaction of alpha diketones and activated thioethers under basic conditions which provides 3,4-disubstituted-thiophene-2,5-dicarboxylic acids upon hydrolysis of the crude ester with aqueous acid. A notable utilization of the Hinsberg procedure was executed in the synthesis of a thiophene analogue of porphyrin.
References
Name Reactions in Heterocyclic Chemistry, Jie-Jack Li, 2005, p. 199-205.
Hofmann elimination
Description
Hofmann degradation or beta-elimination reaction usually means the cleavage of quaternary ammonium hydroxide to form alkene and tertiary amine. In the first step primary, secondary, or tertiary amine is treated with enough methyl iodide to form quaternary ammonium iodide. In the second step, the iodide is converted to the hydroxide by treatment with silver oxide. The third step is the decomposition by pyrolysis. The beta-elimination takes place on the beta-carbon with the least branching (In contrast, E2 elimination of alkyl halides give predominance of the alkene with the greatest amount of branching at the double bond).
References
No references
Hofmann-Löffler-Freytag reaction
Description
The synthesis of pyrrolidine or piperidine derivatives by thermal or photochemical decomposition of the protonated aliphatic N-haloamines is generally known as Hofmann–Löffler–Freytag reaction. Many experimental evidences support the radical mechanism of this reaction, such as the initiation of the reaction by either photo-irradiation or traditional radical initiators and the inhibition of reaction by oxygen. In this reaction, hydrogen abstraction is the chain-propagating step. This reaction has been applied for the preparation of substituted pyrrolidines and piperidines.
References
No references
Horner–Wadsworth–Emmons reaction
Description
The so-called Wittig-Horner reaction is the reaction of aldehydes or ketones with stabilized phosphorus ylides (phosphonate carbanions) leads to olefins with excellent E-selectivity.
References
No references
Huisgen triazole synthesis
Description
Huisgen 1,3-dipolar cycloaddition convenient and straightforward approach for the preparation of a wide range of five-membered ring heterocycles. The Cu(I)-catalyzed, stepwise cycloaddition of an alkyne dipolarophile with a azide as 1,3-dipolar compound exhibits broad scope and provides 1,4-disubstituted 1,2,3-triazoles in excellent yields and high regioselectivity.
References
Angewandte Chemie Int. Ed., 2002, 41, 2596-2599.
Hydration of alkenes
Description
Alkenes can be hydrated quickly under mild conditions without rearrangement of the product. The regiochemistry of water addition to alkenes follows Markovnikov's rule to form alcohols.
References
Comprehensive Organic Reactions in Aqueous Media, Chao-Jun Li, Tak-Hang Chan, 2007, pg.no: 29;
Addition and Elimination Reactions of Aliphatic Compounds, C. H. Bamford, Charles, 1973, pg.no: 300.
Tetrahedron, 2005, 61, 11986-11990;
J. Org. Chem. 2002, 67, 3202-3212;
Hydration of alkynes (Markovnikov's addition)
Description
Alkynes undergo acid-catalyzed Markovnikov addition of water to give enols that immediately tautomerise to form ketones. In generaly, H+, Hg, Pd, Pt, Au... catalysts are used to the form the Markovnikov product and Ru catalyst is used to form the anti-Markovnikov product.
References
Advanced Organic Chemistry, Francis A.CArey, Richard J. Sundberg, 2001, pg.no: 225;
R. W .Bott, C. Eaborn, and D. R. M.Walton, J.Chem. Soc.1965:384;
G.N. Stacy and R.A. Mikulec, Org. Synth. IV: 13 (1963);
W. G. Dauben and D.J. Hart, J. Org. Chem. 42:3789(1977);
D. Caine and F.N Tuller, J. Org. Chem.38:3663(1973);
Organic Chemistry Demystified, D. R. Bloch, pg.no: 197;
Hydrocarbon chemistry, George Andrew Olah, Arpad Molnar, pg.no: 287;
Organic Chemistry (Sie) Carey, pg.no: 371.
Journal of American Chemical Society, 2003, 125, 11925-11935.
Hydration of terminal alkynes (anti-Markovnikov's addition)
Description
The anti-Markovnikov hydration of terminal alkynes to give aldehydes, catalyzed by Ruthenium complexes. In generaly, H+, Hg, Pd, Pt, Au... catalysts are used to the form the Markovnikov product and Ru catalyst is used to form the anti-Markovnikov product.
References
Ruthenium in Organic Synthesis, Shun-lchi Murahashi, 2004, pg.no: 190, 192;
Ruthenium Catalysts and Fine Chemistry, Christian Bruneau, Pierre H. Dixneuf, 2004, pg.no: 132.
Makoto Tokunaga and Yasuo Wakatsuki, AngewChem, 1998, 37, 2867-2869.;
Douglas B. Grotjahn and Daniel A. Lev, JACS, 2004, 126, 12232-12233.;
Aure´lie Labonne, Thomas Kribber, and Lukas Hintermann, OrgLett, 2006, 8, 5853-5856.;
Toshiaki Suzuki, Makoto Tokunaga and Yasuo Wakatsuki, OrgLett, 2001, 3, 735-737.;
J. Am. Chem. Soc. 2004, 126, 12232-12233.
Org Lett, 2006, 8, 5853-5856.
Angew. Chem. Int. Ed. 1998, 37, 2867-2869.
Organic Chemistry, F.A. Carey, 4th Edition, 2000.
Hydrogen bromide addition to alkenes (anti-Markovnikov)
Description
Free-radical addition reaction of alkene with hydrogen bromide to produce alkyl bromide. Peroxides facilitate the formation of a bromine radical and the regioselectivity is anti-Markovnikov.
References
Advanced organic chemistry, Part A, Francis A Carey and Richard J.Sundberg, 2001, Pg.no: 708, 710, 711;
W. J. Bailey and S.S. Hirsch, J. Org. Chem. 28:2894 (1963);
R. Mozingo and L. A. Patterson, Org. Synth. III:576 (1955);
H. O. House, C. –Y. Chu, W. V. Phillips, T. S. B. Sayer, and C. –C. Yau, J. Org. Chem. 42:1709 (1977);
H. L. Goering and L. L. Sims, J. Am. Chem, Soc. 77:3465 (1955);
N.A. LeBel, R. F. Czaja, and A. DeBoer, J. Org. Chem. 34:3112 (1969);
P. D. Readio and P. S. Skell, J. Org. Chem. 31:753 (1966);
H. L. Goering, P. I. Abell, and B. F. Aycock, J. Am. Chem. Soc. 74:3588 (1952).
J. March, Advanced Organic Chemistry, 5th Edition, 2001.
Organic Syntheses, Coll. Vol. 7, p.59 (1990); Vol. 62, p.140 (1984)
Hydrogen halide addition to alkenes (Markovnikov)
Description
Alkenes undergo electrophilic addition reaction with hydrogen halide to produce alkyl halide.
References
Advanced Organic Chemistry, Part A, Francis A Carey and Richard J.Sundberg, 2001, pg.no: 352, 355, 356, 357;
Advanced Organic Chemistry, Part B, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 291;
Y. Pocker and K. D. Stevens, J. Am. Chem, Soc. 91, 4205 (1969);
S. H. Kang, W. J. Kim and Y. B. Chae, Tetrahedron Lett., 1988, 29, 5169;
Comprehensive organic synthesis, Barry M. Trost, Ian Fleming, Martin F. Semmelhack, 1991, Vol 4, pg.no: 279.
J. March, Advanced Organic Chemistry, 5th Edition, 2001.
Hydrogen halide addition to alkynes
Description
Hydrogen chloride, hydrogen bromide, hydrogen iodide add to alkyne yielding alkenyl halide.
References
Organic Chemistry, Raj K Bansal, pg.no: 228;
Advanced Organic Chemistry, Francis A Cary,Richard J. Sundberg, 2007, pg.no: 335;
Hydrocarbon Chemistry, Arpad Molnar, 2003, pg.no: 297;
Unified Course in Chemistry, O.P Agarwal, pg.no: 389.
J. Org. Chem., 1994, 59, 3102-3112.
Hydrolytic carbon monoxide addition to alkynes
Description
Hydrocarboxylation of alkynes to form carboxylic acids in presence of nickel catalyzed compounds.
References
Carbonylation: Direct Synthesis of Carbonyl Compounds, H. M. Colquhoun, D. J. Thompson, M. V. Twigg, 1991, pg. no: 107;
Modern Organo nickel Chemistry, Yoshinao Tamaru, 2006, pg. no: 233;
Comprehensive Organic Reactions in Aqueous Media, Chao-Jun Li, Tak-Hang Chan, 2007, pg.no: 108.
US Patent, 1958, 2-845-451.
Hydroxyation of alkenes with potassium permanganate
Description
Alkenes on treatment with alkaline potassium permanganate at room temperature yields cis-1,2-diols.
References
Organic chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 211;
Invitation to Organic Chemistry, A. William Johnson, 1998, pg.no: 205;
Organic reaction mechanisms, V.K.Ahluwalia, R.K.Parashar, 2003, pg.no: 140;
Organic Reaction Mechanisms, Bansal, 1998, pg.no: 588;
Organic synthetic methods, JamesRoyal Hanson, 2002, pg.no: 100.
Organic Synthesis, 1941, 2, 307.
Hydroxymethylation of phenols
Description
The reaction of phenol with formaldehyde in the presence of alkaline medium results in hydroxymethylation of phenol at ortho and para positions. The reaction is known as Lederer Manasse reaction.
References
Fine chemicals through heterogenous catalysis, Roger A. Sheldon, Herman van Bekkum, 2001, pg. no.175, 176;
Advanced organic chemistry: Structure and mechanisms, Francis A. Carey, Richard J. Sundberg, 2007, pg. no.827;
Adhesion 9, K. W. Allen, 1984, pg. no.5;
Calixarenes: an introduction, Carl David Gutshe, 2008, pg. no.12.
J. Chem. Research (S), 2003, 200-203.
Intramolecular amine alkylation
Description
The intramolecular alkylation of amines yield cyclic amines, usually aziridines, pyrrolidines, piperidines. Usually three-, five-, and six-membered (but not four-membered) rings being easily prepared.
References
No references
Isomerisation of alkenes
Description
Isomerization of alkenes between cis and trans forms.
References
Solid State and Surface Photochemistry, V. Ramamurthy, Kirk S. Schanze, 2000, pg.no: 60,61,63,66;
Addition and Elimination Reactions of Aliphatic Compounds, C. H. Bamford, Charles Frank Howlett Tipper, 1973, pg.no: 300,442;
Liquid crystals: applications and uses, Birendra Bahadur, 1991, pg.no: 365.
J. Org. Chem. 2006, 71, 1055-1059.
Chem. Rev. 2003, 103, 2475-2532.
Isonitril formation
Description
This reaction is an isonitril formation under basic condition using dichlorocarbene as reagent; dichlorocarbene is generated in situ by the phase-transfer method.
References
No references
Isothiocyanate formation from primary aromatic or aliphatic amines
Description
Addition of primary or secondary amines to carbon disulfide yields isothiocyanates. Usually the reaction of aromatic amines with carbon disulfide goes via thiocarbamide, meanwhile the reaction with aliphatic amines goes via dithiocarbamate.
References
No references
Kolbe-Schmitt synthesis
Description
A base-promoted carboxylation of phenols that allows the synthesis of salicylic acid derivatives. This process is known as the Kolbe-Schmitt synthesis. Carboxylation occurs at ortho position.
References
A textbook of organic chemistry, August Bernthsen, Raj K. Bansal, 2003, pg. no.421;
Organic Chemistry (Sie), Carey, pg. no. 1004;
Experiments in Green and Sustainable Chemistry, H. W. Roesky, Dietmar K. Kennepohl, Jean-Marie Lehn, 2009, pg. no. 276-277;
Name reactions: a collection of detailed reaction mechanisms, Jie Jack Li, 2006, pg. no.339;
Comprehensive Practical Organic Chemistry: Preparation and Quantitative Analysis, V. K. Ahluwalia, R. Aggarwal, 2001, pg. no.138;
Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michel G. Ellerd, Frank G. Favaloro, 2005, pg. no.375;
A.Fuerstner, N. Kindler, Tetrahedron Letters 1996, 37, 7005;
W. H.Meek, C. H. Fuchsman, Journal of chemical and engineering data 1969, 14, 388;
A. C. Ragan, J. Staunton, Journal of the chemical society, Chemical communications, 1987, 520.
Chemical Reviews, 1957, 57, 583-620.
Meerwein-Ponndorf-Verley reduction
Description
Reduction of carbonyl groups to alcohols by means of triisopropoxy aluminium.
References
No references
Menshutkin reaction
Description
The so-called Menshutkin reaction is the conversion of tertiary amines to quaternary salts. It is an SN2 substitution between tertiary amines and alkyl halides.
References
No references
Methylation of phenols with diazomethane
Description
Methylation of phenol with diazomethane results in the formation of methylated phenol
References
Concise encyclopedia chemistry, Mary Eagleson, 1994, pg. no.315;
Chemistry of natural products, Sujata V. Bhat, Bhimsen A. Nagasampagi, Meenakshi Sivakumar, 2005, pg. no.62;
Fieser and Fieser's reagents for organic synthesis, Mary Fieser 1980, pg. no.180;
The organic chemistry problem solver, volume 2, Max Fogiel, research and education association, 1986, pg. no.958;
Chemical modification of lignocellulosic materials, David N.-S. Hon, 1996, pg. no.77.
J. Org. Chem., 1968, 33, 223–226.
Milas olefin hydroxylation
Description
cis-hydroxylation of a double bond to a 1,2-diol with hydrogen peroxide and osmium tetroxide as catalyst.
References
Milas, W.A., J. Am. Chem. Soc., 1963, 58, 1302;
Milas, W.A., J. Am. chem. Soc., 1959, 81, 3114;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302 (1936); 59, 543, 2342, 2345 (1937);
N. A. Milas, S. Sussman and H. S. Mason, J. Am. Chem. Soc. 61, 1844 (1939);
N. A. Milas anel L. S. Maloney, ibid. 62, 184l (1940);
J. W. Cook and R. Schoental, J. Chem. Soc. 1950, 47;
W. A. Waters in H. Gilman, Organic Chemistry vol. 4 (John Wiley, New York, 1953), p.1154;
J. F. Eastham, G. B. Milas and C. A. Krauth, J. Am. Chem. Soc. 81, 3114 (1959);
F. D. Gunstone in R. A. Raphael, E. C Talylor, H. Wynberg, Advances in Organic Chemistry vol.1 (Interscience, New York, 1960), p.115;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302 (1936); 59, 543, 2342, 2345 (1937);
N. A. Milas, S. Sussman and H. S. Mason, J. Am. Chem. Soc. 61, 1844 (1939);
N. A. Milas anel L. S. Maloney, ibid. 62, 184l, (1940);
J. W. Cook and R. Schoental, J. Chem. Soc. 1950, 47;
W. A. Waters in H. Gilman, Organic Chemistry vol. 4 (John Wiley, New York, 1953), p 1154;
J. F. Eastham, G. B. Milas and C. A. Krauth, J. Am. Chem. Soc. 81, 3114 (1959);
F. D. Gunstone in R. A. Raphael, E. C Talylor, H. Wynberg, Advances in Organic Chemistry vol.1 (Interscience, New York, 1960), p 115;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302; (1936); 59, 543, 2342, 2345 (1937); 61, 1844 (1939); 62, 1841 (1940);
F. D. Gunstone, Advan. Org. Chem. 1, 115 (1960); P. N. Rylander, Organic Syntheses with Noble Metal Catalysts (Academic Press, New York, 1973) p 60;
NA Milas and Sidney Sussman. J. Am. Chem. Am Chem. Soc. 1936 , 58 , 1302-1303. Soc. 1936, 58, 1302-1303;
Criegee, Ann. 1936, 522, 75;
Organic syntheses based on name reactions, Alfred Hassner, C. Stumer, pg.no: 245.
J . Org. Chem. 1990, 55, 768-770.
Milas olefin hydroxylation
Description
cis-hydroxylation of a double bond to a 1,2-diol with hydrogen peroxide and osmium tetroxide as catalyst.
References
Milas, W.A., J. Am. Chem. Soc., 1963, 58, 1302;
Milas, W.A., J. Am. chem. Soc., 1959, 81, 3114;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302 (1936); 59, 543, 2342, 2345 (1937);
N. A. Milas, S. Sussman and H. S. Mason, J. Am. Chem. Soc. 61, 1844 (1939);
N. A. Milas anel L. S. Maloney, ibid. 62, 184l (1940);
J. W. Cook and R. Schoental, J. Chem. Soc. 1950, 47;
W. A. Waters in H. Gilman, Organic Chemistry vol. 4 (John Wiley, New York, 1953), p.1154;
J. F. Eastham, G. B. Milas and C. A. Krauth, J. Am. Chem. Soc. 81, 3114 (1959);
F. D. Gunstone in R. A. Raphael, E. C Talylor, H. Wynberg, Advances in Organic Chemistry vol.1 (Interscience, New York, 1960), p.115;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302 (1936); 59, 543, 2342, 2345 (1937);
N. A. Milas, S. Sussman and H. S. Mason, J. Am. Chem. Soc. 61, 1844 (1939);
N. A. Milas anel L. S. Maloney, ibid. 62, 184l, (1940);
J. W. Cook and R. Schoental, J. Chem. Soc. 1950, 47;
W. A. Waters in H. Gilman, Organic Chemistry vol. 4 (John Wiley, New York, 1953), p 1154;
J. F. Eastham, G. B. Milas and C. A. Krauth, J. Am. Chem. Soc. 81, 3114 (1959);
F. D. Gunstone in R. A. Raphael, E. C Talylor, H. Wynberg, Advances in Organic Chemistry vol.1 (Interscience, New York, 1960), p 115;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302; (1936); 59, 543, 2342, 2345 (1937); 61, 1844 (1939); 62, 1841 (1940);
F. D. Gunstone, Advan. Org. Chem. 1, 115 (1960); P. N. Rylander, Organic Syntheses with Noble Metal Catalysts (Academic Press, New York, 1973) p 60;
NA Milas and Sidney Sussman. J. Am. Chem. Am Chem. Soc. 1936 , 58 , 1302-1303. Soc. 1936, 58, 1302-1303;
Criegee, Ann. 1936, 522, 75;
Organic syntheses based on name reactions, Alfred Hassner, C. Stumer, pg.no: 245.
N-acylation of azides
Description
This reaction is a direct formation of amide/peptide bonds from carboxylic acids, organic azides and Me3P. This reaction is also called catalytic Staudinger-Vilarrasa reaction.
References
Journal of Organic Chemistry, 2009, 74, 2203-2206.
Nitration of alcohols with nitric acid
Description
Nitration of aliphatic alcohols with nitric acid in presence of sulfuric acid produces alkyl nitrates.
References
Explosive effects and applications, Jonas A. Zukas, William Walters, William P. Walters, 2002, pg. no.141;
A text book of organic chemistry, August Bernthsen, Raj K. Bansal, 2003, pg. no.394;
Canadian journal of chemistry. vol. 34. 1956, 879-884.
Nitration of alkanes
Description
Nitration of alkane to produce nitroalkane selectively.
References
G.A. Olah, H. C. Lin, J. Am. Chem. Soc., 1971, 93, 1259;
R. Atkinson, S. M. Aschmann, W. P. L. Carter, A. M. Winer, J. N. Pitts, J. Phys. Chem., 1982, 86, 4563;
S. Sakaguchi, Y. Nishiwaki,T. Kitamura, Y. Ishii, Angew. Chem. Int. Ed., 2001, 40, 222;
S. Isozaki, Y. Nishiwaki, S. Sakaguchi, Y. Ishii, Chem. Commun., 2001, 1352;
J. Arey, S. M. Aschmann, E. S. C. Kwok, R. Atkinson, J. Phys. Chem. A., 2001, 105, 1020;
Y. Nishiwaki, S. Sakaguchi, Y. Ishii, J. Org. Chem., 2002, 67, 5663;
Modern Oxidation Methods by Jan-Erling Bäckvall, 2004, page.no: 142.
Chem. Commun., 2001, 1352–1353
Nitration of aromatic amines
Description
Nitration of aromatic amines is an aromatic electrophile substitution. Under strong acidic conditions meta orientation is generally observed in the case of arylamines. Under less acidic conditions the free amine activates the ortho/para positions. Primary aromatic amines are usually protected with acetyl chloride or acetic anhydride, the acetamido group is ortho or para directing. Since the nitro group is deactivating, it is usually easy to stop the reaction after one group has entered the ring. The attecking species is nitronium ion (NO2+), which can be formed with HNO3 + H2SO4 or cc. HNO3or N2O5 in CCl4 or with micellaneous etc.
References
No references
Nitration of aromatic hydrocarbons
Description
Aromatic organic compounds are nitrated via an electrophilic aromatic substitution mechanism involving the attack on electron-rich benzene ring by the nitronium ion.
References
Comprehensive Practical Organic Chemistry: Preparation and Quantitative Analysis, V. K. Ahluwalia, R. Aggarwal, 2001, pg. no: 152;
Organic chemistry, Marye Anne Fox, James K. Whitesell, 2004, Pg. no: 556;
Advanced Organic Chemistry: Structure and mechanisms, Francis A. Carey, Richard J. Sundberg, 2007, Pg. no: 793;
The nitro group in organic synthesis, Noboru Ono, 2001, Pg. no: 4.
Tetrahedron Letters 48 (2007) 8659–8664.
Tetrahedron Letters 47 (2006) 4933–4935.
Nitrosation of secondary amines
Description
Nitrosation of secondary amines leading to N-nitrosoamines, which are carcinogenic and mutagenic agents. The nitrosation reactant is nirtosyl cation which is formed in situ. The reaction is usually accomplished by using nitrosating agents such as nitrous acid, NaNO2/HCl, nitrogen oxides (NO, N2O3 or N2O4), peroxynitrite, alkyl nitrites, nitrosyl chloride (NOCI), nitosonium tetrafluoroborate (NOBF4), [NO+-crown-H(NO3)2 -], Fremy’s salt, oxyhyponitrite (N2O3),or Angeli’s salt (Na2N2O3). Primary amines form diazonium salts. Tertiary aliphatic amines undergo cleavage to form N-nitrosoamines and oxocompounds, tertiary aryl amines undergo nitrosation of the ring.
References
No references
Nucleophile acylation with carboxylic acid or anhydride
Description
Acylation of alcohol with acyl anhydride or carboxylic acid.
References
Journal of Molecular Catalysis A: Chemical 181 (2002) 207–213;
Chemistry and chemical reactivity, Volume 2, John C. Kotz, Paul Treichel, John R. Townsend, 2008, pg. no.472;
Invitation to organic chemistry, A. William Johnson, 1999, pg. no.556;
E. J. Chem., 5, 2008, 641-647;
General organic and biological chemistry, Kenneth W. Raymond, 2009, pg. no.266;
Comprehensive Practical Organic Chemistry: Preparation and Quantitative Analysis, V. K. Ahluwalia, R. Aggarwal, 2001, pg. no.101;
J. Am. Chem. Soc., 103, 5972, (1981).
Nucleophilic aromatic substitution (SN2)
Description
Aryl halides undergo nucleophilic aromatic substitution under certain conditions, where the reactive agent is an electron donor, while the leaving group is a halogen ion. The larger the number of electron withdrawing substituents on the ring, especially in the positions ortho and para to the point of substitution, the greater the rate of reaction.
References
Organic chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no.858;
Organic chemistry demystified, D. R. Bloch, 2006;
Advanced organic chemistry: reactions and synthesis, Francis A. Carey, Richard J. Sundberg, pg. no.724;
Microscale organic laboratory: with multistep and multiscale syntheses, Dana W. Mayo, Ronald M. Pike, David C. Forbes, 2010, pg. no.385;
Principles of organic synthesis, Richard Oswald Chandler Norman, James M. Coxon, 1993, pg. no.400, 401;
Advanced organic chemistry: reactions and mechanisms, Singh, 2007, pg. no.332;
Comprehensive organic synthesis: additions and substitutions at c-c pi bonds, M. Trost, Ian Fleming, Martin F. Semmelhack, 1991, pg. no.433;
Organic Chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no.859.
Oppenauer oxidation
Description
A mild oxidation of alcohols to aldehydes or ketones, using metal (Al, K) alkoxydes and a aldehyde or ketone.
References
No references
Oxidation of alcohols
Description
Alcohols can be oxidized to aldehydes or carboxylic acids or to ketons.
References
Reactions and syntheses in the organic chemistry laboratory By Lutz-Friedjan Tietze, Theophil Eicher, Ulf Diederichsen, Andreas Speicher, 2007, pg. no.216;
Advanced Organic Chemistry Part B: Reactions and synthesis By Francis A. Carey, Richard J. Sundberg, 2007, pg. no.1068;
Reagents for organic synthesis, Volume 1, Louis Frederick Fieser, 1969, pg. no.142;
Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Jie Jack Li, 2009, pg. no.305
Oxidation of alcohols to aldehydes and ketones: a guide to current common practice, Gabriel Tojo, Marcos Fernandez, 2006, pg. no.15, 23, 24;
Organic Synthesis: concepts and methods, Jorgen-Hinrich Fuhrhop, Guangtao Li, pg. no.189.
Oxidation of aldehydes
Description
The reaction is done under acidic conditions and the aldehyde is oxidized to a carboxylic acid. (Under alkaline conditions a salt is formed instead).
References
No references
Oxidation of alkanes to alcohols
Description
Oxidation reaction of alkanes to produce alcohols selectively.
References
K. Wiberg, G. Foster, J. Am. Chem. Soc., 1961, 83, 423;
S. Yiu, Z. Wu, C. Mak, T. Lau, J. Am. Chem. Soc., 2004, 126, 14921;
B.C. Bales, P. Brown, A. Dehestani, J.M. Mayer, J. Am. Chem. Soc., 2005, 127, 2832;
T. M. Hellmann, G.A. Hamilton, J. Am. Chem. Soc., 1974, 96, 5, 1530;
K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, T. Horaguchi, J. Chem. Soc. Perkin Trans. I., 2001, 3230;
US 5017731, 1991;
Ruthenium in Organic Synthesis, Shun-Ichi Murahashi(Ed.) , 2004, pg.no: 69, 83;
Green Chemistry and Catalysis, Roger Arthur Sheldon, Isabel Arends, Ulf Hanefeld, 2007, pg.no: 163.
Oxidation of alkanes to ketones
Description
Oxidation reaction of alkanes to produce ketones selectively.
References
C.C. Hobbs, B. Houston, J. Am. Chem. Soc., 1954, 76, 1254;
W.F. Sager, A. Bradley, J. Am. Chem. Soc., 1956, 78, 1187;
Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama, Y. Nishiyama, J. Org. Chem., 1996, 61, 4520;
S. Yiu, Z. Wu, C. Mak, T. Lau, J. Am. Chem. Soc., 2004, 126, 14921.
Oxidation of alkenes with peracids
Description
Oxidation of alkenes with peracid yields epoxides.
References
Oxidation and Reduction in Organic Synthesis, Timothy J.Donohoe, pg.no: 14;
Modern Methods of Organic Synthesis, William Carruthers and Iain Coldham, 2004, pg.no: 332, 333;
Synthetic Approaches in Organic Chemistry, Raj K. Bansal, pg.no: 72;
Asymmetric Organocatalysis, Albrecht Berkessel, Harald Gröger, David MacMillan, pg.no: 292.
J. Org. Chem. 1999, 64, 196-201.
Oxidation of alkenes with potassium permanganate
Description
Acidified potassium permanganate solution oxidises alkenes to carboxylic acids.
References
Organic Chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 213;
Organic Chemistry, Marye Anne Fox, James K. Whitesell, 2004, pg.no: 501.
J. Org. Chem., 1977, 42, 3749-3753.
Oxidation of alkynes with potassium permanganate(basic medium)
Description
Alkynes on treatment with alkaline potassium permanganate undergo oxidative cleavage at triple bond to form carboxylic acids. The position of the triple bond determines the resulting carboxylic acids.
References
Organic Reaction Mechanisms, V. K. Ahluwalia, R. K. Parashar, 2003, pg.no: 142;
Organic Chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 261.
Vogel's Textbook of Practical Organic Chemistry, fifth edition, p. 670.
J Org Chem, 1979, 44, 2726-2730.
J Org Chem, 1985, 50, 4306-4309.
Oxidation of alkynes with potassium permanganate(neutral medium)
Description
Internal alkynes on oxidation with potassium permanganate under mild conditions forms diketones.
References
Organic Reaction Mechanisms, V. K. Ahluwalia, R. K. Parashar, 2003, pg.no: 142;
Advanced organic chemistry, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 1075;
Hydrocarbon chemistry, Árpád Molnár, 2003, pg.no: 489.
J Org Chem, 1979, 44, 1574.
Oxidation of alpha methyl aromatic hydrocarbons with KMnO4 to benzoic acid
Description
Alkyl benzenes undergo oxidation with strong oxidizing agent, KMnO4. The benzene ring is unchanged but the alkyl group is oxidized. All carbons of the alkyl group except that attached to the ring are oxidized to CO2. The carbon attached to the ring is oxidized to the highest oxidation state possible (COOH group) with out breakage of the bond to the aromatic ring.
References
Comprehensive Practical Organic Chemistry, V.K. Ahluwalia, R. Aggarwal, 1905, Pg. no: 159-160;
Organic Chemistry, Manju Mehta, 2005, Pg. no: 291;
A textbook of organic chemistry, August Bernthsen, Raj K. Bansal, Ed. 4, 2003, Pg. no: 314;
The organic chemistry problem solver, Max Fogiel, 2001, Pg. no: 402-403;
Schaum's outline of theory and problems of general, organic, and biological, George G. Odian, Ira Blei, 1994, Pg. no: 237.
Organic Synthesis, 1955, 3, p791.
Oxidation of anilines to ortho quinones
Description
Ortho and para aromatic diamines are easily oxidized to ortho- and para-quinones. Either or both NH2 groups can be replaced by OH groups to give the same products, but for the preparation of ortho-quinones only OH groups are normally satisfactory. The reaction has been successfully carried out with other groups para to OH or NH2: halogen, OR, Me, f-Bu, and even H. Many oxidizing agents have been used: acid dichromate, silver oxide, silver carbonate, lead tetraacetate, HIO4, dimethyl dioxirane, and atmospheric oxygen etc. A particularly effective reagent for rings with only one OH or NH2 group is (KSO3JN—O- (dipotassium nitrosodisulfonate; Fremy's salt), which is a stable free radical. Phenols, even some whose para positions are unoccupied, can be oxidized to ortho-quinones with diphenylseleninic anhydride.
References
No references
Oxidation of anilines to para quinones
Description
Ortho and para aromatic diamines are easily oxidized to ortho- and para-quinones. Either or both NH2 groups can be replaced by OH groups to give the same products, but for the preparation of ortho-quinones only OH groups are normally satisfactory. The reaction has been successfully carried out with other groups para to OH or NH2; halogen, OR, Me, f-Bu, and even H. Many oxidizing agents have been used: acid dichromate, silver oxide, silver carbonate, lead tetraacetate, HIO4, dimethyl dioxirane, and atmospheric oxygen etc. A particularly effective reagent for rings with only one OH or NH2 group is (KSO3JN—O- (dipotassium nitrosodisulfonate; Fremy's salt), which is a stable free radical. Phenols, even some whose para positions are unoccupied, can be oxidized to ortho-quinones with diphenylseleninic anhydride.
References
No references
Oxidation of phenols to ortho or para quinones
Description
Oxidation of phenols with K2Cr2O7/ H2SO4 or AgO yields conjugated dicarbonyl compounds called quinones.
References
Organic chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no. 813;
General organic and biological chemistry, Kenneth W. Raymond, 2009, pg. no.271;
General guidelines for synthesis and purification of Quinone compounds, pg. no.1, 2.
Organic Synthesis, 1941, 1, p. 482.
Oxidation of tertiary amine to amine oxide
Description
Oxidation reaction of tertiary amines to amine oxides using oxidating agent.
References
No references
Oxidation of vicinal diols to aldehydes or ketones
Description
1, 2- diols (vicinal diols) undergo oxidation to form aldehydes or ketones.
References
Org. Lett., 1999, 1 (5), pp 713–715;
Handbook of Reagents for Organic Synthesis: Reagents for high-throughput solid-phase and solution-phase organic synthesis by Peter Wipf, 1999, pg. no.309;
Principles of organic synthesis, Richard Oswald Chandler Norman, James M. Coxon, 1993, pg. no.616;
Organic chemistry, Dhawan, 2007, pg. no.7-25;
Organic chemistry demystified, D. R. Bloch, 2006, pg. no.310;
Organic chemistry, Thomas N. Sorrell, 2006, pg. no.343.
Ozonolysis of alkenes
Description
Ozone is an electrophilic reagent that reacts with carbon-carbon double bonds by a 1,3-dipolar cycloaddition reaction followed by rearrangement reaction to form ozonides. The resulting ozonides can be cleaved oxidatively or reductively to carboxylic acids, ketones, aldehydes or alcohols. The nature of the products formed depends on the structure of the alkene.
References
Oxidation and Reduction in Organic Synthesis, Timothy J.Donohoe, 2003, pg.no: 37;
Organic chemistry, Marye Anne Fox, James K. Whitesell, pg.no: 503;
Modern Methods of Organic Synthesis, William Carruthers and Iain Coldham, 2004, pg.no: 360.
Organic Letters 2006, 8, 3199-3201.
Paal-Knorr pyrrole synthesis
Description
Paal-Knorr pyrrole synthesis is the condensation of a 1,4-dicarbonyl compound with an excess of a primary amine or ammonia to give a pyrrole.
References
Tetrahedron, 2006, 47, 5383-5387.
Paal-Knorr thiophene synthesis
Description
Paal-Knorr synthesis allows to generate 5 membered heterocyclic rings such as thiophenes, furans or pyrrols from 1,4-diketones. Thiophene synthesis is a condensation reaction of 1,4-dicarbonyl compound in the presence of an excess of a source of sulfur such as phosphorous pentasulfide or Lawesson's reagent - the latter acts as sulfurizing agents as well as dehydrating agents.
References
Journal of Organic Chemistry, 2008, 73, 3377-3383.
Petasis reaction
Description
The Petasis Reaction (or the so-called boronic acid Mannich reaction) is a multicomponent reaction for coupling of an amine, aldehyde, and vinyl- or aryl-boronic acid to form substituted amines. The direct reaction with glyoxylic acid leads to unnatural α-amino acids in a single step, while avoiding the appearance of toxic side products.
References
No references
Phenol formation from primary anilines
Description
Conversion of aniline to phenol can be achieved by treating aniline with NaNO2+ acid (diazotisation) than treat it with base like NaOH/KOH or simple H2O.
References
No references
Pictet Spengler isoquinoline synthesis
Description
The Pictet-Spengler reaction is one of the key methods for construction of the isoquinoline skeleton. This reaction involves the condensation of a beta-arylethylamine with an aldehyde, ketone, or 1,2-dicarbonyl compound to give the corresponding tetrahydroisoquinoline. These reactions are generally catalyzed by protic or Lewis acids, although numerous thermally-mediated examples are found in the literature. Aromatic compounds containing electron-donating substituents are the most reactive substrates for this reaction.
References
Chinese Chemical Letters, 2004, 15, 505-507.
Reaction of alkynes with oxo compounds (Reppe like reaction)
Description
Oxo compounds participate in acetylide addition to afford the corresponding propargyl alcohols.
References
Industrial organic chemicals, Harold A. Wittcoff, Bryan G. Reuben, Jeffrey S. Plotkin, 2004, pg.no: 352;
Acetylene chemistry, François Diederich, Peter J. Stang, Rik R. Tykwinski, 2005, pg.no: 104, 116, 117, 118, 119, 121, 123, 124.
Reaction of amines with alcohols
Description
The alkylation of amines by alcohols with loss of water is a thermodynamically favored process where the loss of a carbon-oxygen bond for forming a carbon-nitrogen bond is compensated by the gain of an oxygen-hydrogen bond from a nitrogen-hydrogen bond. The reaction can be performed using heterogeneous or homogeneous catalysis.
References
No references
Reaction of primary aliphatic amines with nitrous acid
Description
Low molecular weight primary aliphatic amines would react easily with nitrous acid to form primary alcohols. The oxidative deamination of aliphatic amines by nitrous acid results in alcohol, and nitrogen gas and water as side products.
References
No references
Reduction of alkyl halides (Zn/H+,LiAlH4,Pd/C,HI)
Description
Alkyl halides undergo reduction by suitable reducing agents such as LiAlH4, Zn/H+, Pd/C & HI/red phosphorus to form corresponding alkanes.
References
Comprehensive organic synthesis: Selectivity, Strategy, and Efficiency in Modern Organic Chemistry, Barry M. Trost, Ian Fleming,1991, pg. no: 795, 803;
Organic chemistry, 8th edition, Solmons G, 2009, pg. no:51;
The essentials of organic chemistry, Max Fogiel, Research and education association, 1995, pg. no:14;
Comprehensive organic functional group transformations, Alan R. Katritzky, Otto Meth-Cohn, Charles Wayne Rees, 1995, pg. no:3;
A text book of organic chemistry, August Bernthsen, Raj K Bansal, pg. no:161;
Organic chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no:145;
Chemistry, Arun Mittal, 2007, pg. no:394;
Organic chemistry I, Max Fogiel, research and education association, 1994, pg. no:32.
Mandai, McMurray, J Org Chem, 2007, 72, 6556-6561.
J. Org. Chem. 1982,47, 276-280.
Reduction of carboxylic acids to primary alcohols
Description
Carboxylic acids are reduced to primary alcohols by several catalysts, the most common and powerful reducing agent is lithium aluminum hydride. Aldehyde is formed first and then a primary alcohol. Because LiAlH4 reacts rapidly with aldehydes, it is impossible to stop at the halfway stage. LiAlH4 reacts violently with water and so the reactions are carried out in solution in dry solvent (Et2O or THF). The reaction happens at room temperature; the product is a complex aluminium salt that is converted into the alcohol by acidic workup.
References
Indian Pat. Appl., 2007CH01104, 06 Feb 2009, Chakrabarti, Dhurjati Prasad et al
Reduction of nitriles
Description
Aliphatic or aromatic nitriles can be reduced to primary amine with a suitable chemical reagent. Typical reagent is LiAlH4 in ether solvent followed by aqueous work-up. Catalytic hydrogenation (H2 / catalyst) can also be used giving the same products. Nitriles can also be reduced to aldehydes. One method is called the Stephen aldehyde synthesis.
References
Green Chemistry, 2010, 12(1), 87-93.
Reduction of nitro arenes to azo arenes
Description
Reduction of aromatic nitro compound with different reducing agents yields aryl azo compound.
References
Treatise on general and industrial organic chemistry, Molinari Ettore, 2009, pg. no.565;
Tellurium in organic synthesis, Nicola Petragnani, Hélio A. Stefani, 2007, pg. no.122;
Comprehensive organic synthesis: selectivity, strategy, and efficiency in Modern Organic Chemistry, Barry M. Trost, Ian Fleming, 1991, pg. no.364;
Bull. Chem. Soc. Jpn., 69, No.2 (1996);
Electrolytic preparations: Exercises for use in the laboratory by chemists, Robert Salmon Hutton Karl Elbs, 2009, pg. no.79.
Organic Synthesis, 1955, 22, p28.
Reduction of nitro compounds to amines or anilines
Description
The reduction of nitro compounds in presence of metal catalyst (Fe/HCl, H2/Raney Ni, Sn/HCl, SnCl2/HCl etc.) to give primary amines.
References
Organic chemistry II, Max Fogiel, 2000, pg. no.79;
The nitro group in organic synthesis By Noboru Ono,2001, pg. no. 172, 174;
Organic chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no.788;
Organic chemistry, Dhawan, 2007, pg. no.9-71.
Teaching of Chemistry Pr By P.b.samnani, 2009, pg. no.102;
Use of polymer-supported amines in the catalytic nitr-aldol reaction of nitroalkanes with aldehydes, Francisco Palacios, Jesus M. de los Santos, and Domitila Aparicio, 28 th June 2005, pg. no.5;
E-Journal of chemistry, vol 5, pp. 914-917, October 2008.
J. Org. Chem. 2009, 74, 6960–6964.
Ring closure by halogen elimination from alkyl halides
Description
Dihaloalkanes (two halogens are present at two terminals) on reaction with Na or Zn metal undergo intramolecular cyclization to produce cycloalkanes.
References
Hydrocarbons (Alkanes, Alkenes And Alkynes), Amit Arora, 2006, pg. no. 2;
The essentials of organic chemistry, Max Fogiel, Research and Education Association, pg. no. 48;
Organic Chemistry for advanced students, Julius Berend Cohen, 2009, pg. no. 189;
Organic Chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no. 173
Organic Syntheses, 1973, 5, 328; 1964, 44, 30.
Ritter reaction of alkenes
Description
Synthesis of amides from nitriles and alkenes under strongly acidic media.
References
J.J. Ritter, P.P. Minieri, J. Am. Chem. Soc., 1948, 70, 4045;
J.J. Ritter, J. Kalish, J. Am. Chem. Soc., 1948, 70, 4048;
L.S. Hegedus, T.A. Mulhern, H. Asada, J. Am. Chem. Soc., 1986, 108, 20, 6224-6228;
C.L. McCormick, C.B. Johnson, J. Macromol. Sci.-Chem.A. 1990, 27, 5, 539;
W.M. Samaniego, Tetrahedron Lett., 1994, 35, 6967;
M. Camail, A. Margaillan, S.Turet, J.L. Vernet, Eur. Polymer J., 1998, 34, 11;
V. Nair, R. Rajan, N.P. Rath, Org. Lett., 2002, 4, 1575-1577;
L. Castellanos, C. Duque, J. Rodríguez, C. Jiménez, Tetrahedron, 2007, 63, 7, 1544-1552;
Encyclopedia of Chemical Processing and Design, John J. McKetta, William Aaron, 1997, pg.no: 185;
Name Reactions, Jie Jack Li, pg.no: 501.
J. Org. Chem. 2009, 74, 2207–2209.
Eur. J. Org. Chem. 2007, 4642–4645.
SN1 substitution of alkyl halides
Description
In the SN1 reaction, a planar carbenium ion is formed first, which then reacts further with the nucleophile. Since the nucleophile is free to attack from either side, this reaction is associated with racemization. SN1 reactions work best with weak nucleophiles. Typical polar protic solvents include water and alcohols, which will also act as nucleophiles.
References
Chemistry for pharmacy students: general, organic and natural product chemistry, Satyajit D. Sarker, Lutfun Nahar, 2007, pg. no. 233;
Organic Chemistry, Joseph M. Hornback, 2005, Ed. 2, pg. no. 278;
Advanced Organic Chemistry: Reactions and Mechanisms, Singh, pg. no. 97;
Organic Chemistry, 8th Edition, Solomons & Fryhle, pg. no. 257;
Organic Chemistry (Sie), Carey, pg. no. 334;
Organic Chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no. 343.
Orgnic Letters, 2002, 4, 343-345.
SN2 substitution of alkyl halides
Description
SN2 is a bimolecular, nucleophilic substitution reaction. In a bimolecular mechanism, the attack of nucleophile on sp3 hybridized carbon of alkyl halide and removal of halide ion (leaving group) occurs simultaneously in a single step. Thus, nucleophile has no other option but to attack the carbon from a side opposite to halogen (leaving group). SN2 mechanism involves the inversion of configuration (also known as Walden Inversion).
References
Advanced organic chemistry: reactions and mechanisms, Singh, 2007, pg. no. 94, 98, 104;
Organic chemistry, 8th edition, Solomons & Frryhle, 2009, pg. no. 245, 250, 251;
Organic chemistry, Marye Anne Fox, James K.Whitesell, 2004, pg. no. 42;
Modern physical organic chemistry, Eric V. Anslyn, Dennis A. Dougherty, pg. no. 638;
Organic chemistry (Sie), Carey, 2008, pg. no. 338;
Organic chemistry, J. William Suggs, 2001, pg. no.123.
Schotten-Baumann reaction
Description
The nucleophilic acyl substitution reaction of carboxylic acids and amines is a method for amide synthesis; in practice amides are more readily prepared from the more reactive acyl chlorides.
References
Synthetic Communication, 2009, 39, 2694-2701.
Schotten-Baumann reaction with phenols
Description
Phenol reacts with acid chlorides (or acid anhydrides) in alkali solution to form phenylesters (acylation). This reaction is called Schotten-Baumann reaction.
References
Practical pharmaceutical chemistry - II, Dr. A. V. Kasture, Dr. S. G. Wadodkar, 2008, pg. no.53;
Comprehensive practical organic chemistry: Preparation and quantitative analysis, V. K. Ahluwalia, R. Aggarwal, 2001, pg. no.101;
Organic Chemistry (Sie), Carey, 2008, pg. no.1001;
Comprehensive Practical Organic Chemistry: Qualitative Analysis, V.K. Ahluwalia, S. Dhingra, 2004, pg. no. 57;
Practical organic chemistry, Frederick George Mann, Bemard Charles Saunders, 1960, pg. no 110.
Sulfation of alcohols with sulfuric acid
Description
Sulfation of alcohols with sulfuric acid to produce alkyl hydrogen sulfates.
References
Aliphatic organic chemistry, Amit Arora, 2006, pg. no.84;
Organic Chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no.437;
Chemistry, Kenneth W. Whitten, Raymond E. Davis, M. Larry Peck, George G. Stanley, 2009, pg. no.1017;
Polysaccharides: structural diversity and functional versatility, Severian Dumitriu, 2005, pg. no.1181;
Characterization of organic compounds by chemical methods: an introductory laboratory text book, Terence C. Owen, 1969, pg. no.55.
BAYER CROPSCIENCE AG Patent: WO2007/22900 A1, 2007;
Sulfonation of aromatic amines
Description
Arylamines are very reactive toward electrophilic aromatic substitution. It is customary to protect arylamines as their N-acyl derivatives before carrying out ring nitration, chlorination, bromination, sulfonation, or Friedel–Crafts reactions.
References
No references
Sulfonation of aromatic hydrocarbons
Description
Reaction of aromatic hydrocarbons with sulfuric acid produces corresponding sulfonic acids. It is an electrophilic substitution reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group.
References
Synthetic approaches in organic chemistry, Raj K. Bansal, 1996, pg. no: 370;
Riegel's handbook of industrial chemistry, Emil Raymond Riegel, James Albert Kent, 2003 pg. no: 922;
Chlorosulfonic acid: a versatile reagent, Richard James William Cremlyn, Royal Society of Chemistry (Great Britain), 2002, pg. no: 45, 46:
J Am Chem Soc, 1982, 47, 4075-4081.
Symmetric coupling of 1-alkynes
Description
Terminal alkynes or 1-trimethylsilyl alkynes can be coupled by heating with stoichiometric amounts of cupric salts in pyridine or similar base to produce symmetrical diynes in high yields.
References
Comprehensive organic functional group transformations, Alan R. Katritzky, Otto Meth-Cohn, Charles Wayne Rees, 1995, pg. no: 1035;
Name Reactions, Jie Jack Li, 2006, pg.no: 265;
Name Reactions and Reagents in Organic Synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, Frank G. Favaloro, Jr, 2005, pg.no: 225;
Acetylene Chemistry, François Diederich, Peter Stang, Rik R. Tykwinski, 2006, pg.no: 374;
M.H.Haley, M.L.Bell, S.C.Brand, D.B.Kimball, J.J.Pak, W.B.Wan,Tetrahedron Letters 1997,38,7483;
F.Jung, A.Berger,J.-F.Biellmann, Organic Letters 2003, 5,383.
Symmetric coupling of di-alkynes
Description
Oxidative coupling of terminal di-alkynes with a stoichiometric amount of a copper(II) salt in pyridine.
References
Modern supramolecular chemistry: strategies for macrocycle synthesis, François Diederich, Peter J. Stang, Rik R. Tykwinski, 2008, pg.no: 190;
Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, 2005, pg.no: 224, 225;
S.Hoger, K.Bonard, L.Karcher, A.D.Meckenstock, Journal of Organic Chemistry 2000, 65, 1588;
F.Toda, Y.Tokumaru, Chemistry Letters 1990, 987;
Acetylene Chemistry, François Diederich, Peter Stang, Rik R. Tykwinski, 2006, pg.no: 346, 374, 375;
Some modern methods of organic synthesis, W. Carruthers, 1971, pg.no: 50.
J. Org. Chem. 2006, 71, 4544-4548.
Synthesis of acid anhydrides
Description
Acid anhydrides are one of the most reactive carboxylic acid derivatives and are synthesized by nucleopilic substitution reaction.
References
No references
Synthesis of acid bromides
Description
Synthesis of acyl bromides from carboxylic acids is a nucleophylic acyl substitution reaction. PBr3, as a strong reducing and the most common brominating agent converts carboxylic acids to carboxylic acid bromides. An acyl bromide can readily exist in the enol form, and this tautomer is rapidly brominated at the α-carbon. Other possible brominating agents: PBr5, Br2, NBS etc. Acyl bromides are rarely made in comparison with acyl chlorides.
References
No references
Synthesis of acid chlorides
Description
Synthesis of acyl chlorides from carboxylic acids by treating them with thionyl chloride (SOCl2), or phosphorus trichloride (PCl3), or phosphorus pentachloride (PCl5) is a nucleophylic acyl substitution reaction. The reaction is usually catalyzed by dimethylformamide.
References
No references
Synthesis of cyclic anhydrides
Description
Cyclic anhydrides containing five- and six-membered anhydride rings are readily prepared from their corresponding dicarboxylic acids. This reaction is so facile, that in some cases it occurs on heating the dicarboxylic acid. POCl3, P2O5 or acetic anhydride can also be used for the formation of cyclic anhydrides. Anhydrides are typically not target molecules, but rather they are used as intermediates for the synthesis of other organic members such as esters and amides for the industrial applications include dyes, pharmaceuticals, pesticides, plastics, fibers, curing agents, plasticizers and many others. Phthalic anhydride is a versatile intermediate in organic chemistry, in part because it is bifunctional and cheaply available.
References
No references
Tetrazole synthesis
Description
Azide ions (e.g. sodium azide in DMF) react with nitriles in a [3+2] cycloaddition with formation of 5-substituted 1-H tetrazoles. Cycloaddition of alkyl-, aryl- or trimethylsilyl azide with nitriles or isonitriles yields 1,5- and/or 2,5-disubstituted tetrazoles.
References
European Journal of Organic Chemistry, 2003, (5), 885-893.
Tosylation with Koser's reagent
Description
Vic-bis tosylation of alkenes by means of hydroxytosyloxyiodobenzene.
References
Koser, G.F., J. Org. Chem., 1977, 42, 1476;
Neiland, O., J. Org. Chem. USSR(Eng.), 1970, 6, 889;
Koser, G.F., J. Org. Chem., 1980, 45, 1542;
Koser, G.F., J. Org. Chem., 1984, 49, 2462;
Papoutsis I. Spyroudis S. Varvoglis A, Tetrahedron, 1998, 54, 1005-1012;
Wirth Yusubov, Org. Lett., 2005, 7, 519;
Organic syntheses based on name reactions, Alfred Hassner, C. Stumer, 2002, pg.no: 206;
Cyclopropanation of alkenes using hypervalent iodine reagents, Andreas S. Biland,a Sabine Altermann,b and Thomas Wirtha,b;
Hirt, U. H.; Spingler, B.; Wirth, T. J. Org. Chem. 1998, 63, 7674.
Transesterification reaction
Description
The reaction is an interchange of an organic ester groups into another ester of the same acid with an alcohol in the presence of a acid, base or enzyme catalysis. The acid catalyzed mechanism for this transesterification simply consists of adding one alcohol and eliminating the other.
References
Synthetic Communications, 2010, 40(11), 1670-1676.
Ullmann reaction
Description
The Ullmann reaction is the synthesis of biaryls from aryl halides via copper-catalyzed coupling. In this reaction, the first step is the oxidative addition of the copper into the aryl halide. The copper (I) aryl species then undergoes oxidative coupling with another equivalent of the aryl halide resulting in a biaryl copper compound. Reductive elimination follows resulting in the formation of the carbon- carbon bond. The reaction is limited to electron deficient aryl halides and requires harsh reaction conditions.
References
F. Ullmann, Justus Liebigs Ann. Chem., 1904, 232, 38;
F. Ullman, Bielecki, Ber., 1901, 34, 2174;
R.C. Fuson, E.A. Cleveland, Organic Syntheses, Coll. Vol. 3, p.339; Vol. 20, p.45;
F. Ullmann, P. Sponagel, Ber, 1946, 38, 407;
P.E. Fanta, Chem. Revs., 1946, 38,139;
P.E. Fanta,Synthesis, 1974, 9;
L.M. Stark, X.-F. Lin, L.A. Flippin, J. Org. Chem., 2000, 65, 3227;
K.D. Belfield, K.J. Schafer, W. Mourad, B.A. Reinhardt, J. Org. Chem., 2000, 65, 4475;
S. Venkatraman, C.-J. Li, Tetrahedron Lett, 2000, 41, 4831;
J.M. Farrar, M. Sienkowska, P. Kaszynski, Synth. Commun, 2000, 30, 4039;
D. Ma, C. Xia, Org. Lett., 2001, 3, 2583;
E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, P.J. Reider, Org. Lett., 2002, 4, 1623;
A. Hameurlaine, W. Dehaen, Tetrahedron Lett, 2003, 44, 957;
Name Reactions for Homologation, Jie Jack Li, E. J. Corey, 2009, Pg. no: 258- 259;
Synthesis of biaryls, Ivica Cepanec, 2004, Pg. no: 10, 13-15, 15-16, 32;
Name Reactions for Homologation, Jie Jack Li, E. J. Corey, 2009, Pg. no: 261.
Advances in heterocyclic chemistry, Alan R. Katritzky, 1984, Pg. no: 121;
Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, 2005, Pg. no: 663;
A. I. Meyers, J. J. Willemsen, Tetrahedron Letters 1996, 37, 791.
Wacker-Tsuji olefine oxidation
Description
Oxidation of alkenes to ketones in the presence of Pd(II) catalysts. The oxidation of ethylene to acetaldehyde employing palladium chloride and cupric chloride as catalysts and molecular oxygen as oxidant. The reaction has been extensively developed for the oxidation of terminal alkenes to methyl ketones.
References
F.C. Phillips, Amer. Chem. J., 1984, 14, 255;
J. Tsuji, et al., Tetrahedron Lett., 1982, 23, 2679;
J. Smidt, (Wacker), Angew. Chem., 1959, 71, 176;
J. Tsuji, et al. Synthesis, 1984, 369;
D.D.M. Wayner, J. Org. Chem., 1990, 55, 2924;
Application to hydroxy-alpha,beta-unsaturated esters: S. X. Auclair et al., Tetrahedron Letters 33, 7739 (1992);
Use of a multicomponent catalytic system: E. Monflier et al., ibid. 36, 387 (1995);
Synthetic applications: M. Romero et al., ibid. 35, 3255 (1994);
L.A. Paquette, X. Wang, J. Org. Chem. 59, 2052 (1994);
Reviews: L. S. Hegedus, Comp. Org. Syn. 4, 552-559 (1991);
J. Tsuji, ibid. 6, 449-468;
J. Smidt et al., Angew. Chem. Int. Ed. 1, 176 (1959);
S. X. Auclair et al., Tetrahedron Letters 33, 7739 (1992) ;
E. Monflier et al. Tetrahedron Letters, 36, 387 (1995) ;
M. Romero et al., Tetrahedron Letters, 35, 3255 (1994);
L. A. Paquette, X. Wang, J. Org. Chem. 59, 2052 (1994) ;
L. S. Hegedus, Comp. Org. Syn. 4, 552-559 (1991);
J. Tsuji, Comp. Org. Syn. 6, 449-468(1991);
J. Tsuji, M. Minato, Tetrahedron Letters, 28, 32, 1987, 3683-3686;
J. Tsuji, H. Nagashima,K Hori, Tetrahedron letters, 23, 26, 1982, 2679-2682;
G. Cum, R. Gallo, S. Ipsale, A. Spadaro, J. Chem. Soc. Chem. Commun., 22, 1985, 1571-1573;
Modern Methods of Organic synthesis, William Carruthers and lain Coldham, 2004, pg.no: 366, 367;
Name Reactions of Functional Group Transformations, Jie Jack Li, E.J.Corey, 2007, pg.no: 319;
Advanced Organic Chemistry, Francis A. Carey, Richard J. Sundberg, 2007, pg.no; 711;
Hydrocarbon chemistry, Goerge A Olah, Arpad Molnar, 2003, pg.no: 526.
Water addition to carbonyl compounds
Description
Nucleophilic addition of water to carbonyl group of aldehydes and ketones is an equilibrium reaction which depends strongly on the structure and steric hindrance of the carbonyl compoound. Electron withdrowing groups can increase the extent of hydration. The reaction goes via either acid or base catalysis. The extent of hydration decreases as the number of alkyl groups on the carbonyl increase, thats why aldehydes react faster than ketones. Aryl aldehydes and ketones have relatively unfavorable hudration equlibria. The relative rate of addition cab be predicted from the trends in equlibrium constants. Hydrates are usually stable in water solution and decompose on distillation.
References
No references
Williamson ether synthesis
Description
In Williamson synthesis, ethers can be prepared by reaction of alkoxide (alcoholate) or phenoxide with an alkyl halide.
References
A text book of organic chemistry for students of medicine and biology, Elmer Verner McCollum, 2008, pg. no:51;
Organic chemistry, 8th edition, Solomons & Fryhle, 2009, pg. no:512;
Organic chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no: 445;
The organic chemistry problem solver, volume 2, Max Fogiel, research and education association, 1994, pg. no. 491, 492;
Microscale organic laboratory: With multistep and multiscale syntheses, Dana W. Mayo, Ronald M. Pike, David C. Forbes, 2010, pg. no.321;
Organic chemistry (Sie), Carey, 2008, pg. no.670, 671.
Organic Syntheses, 1990, 7, p386.
Wittig reaction
Description
The Wittig reaction uses phosphorus ylides (Wittig reagents) to convert aldehydes and ketones to alkenes. The double bond connects the carbon of the original C=O group of the aldehyde or ketone and the negatively charged carbon of the ylide. The reaction is carried out under strong basic conditions. The most attractive feature of the Wittig reaction is its regiospecificity. With simple ylides this results in almost exclusively the Z-alkene product. With semistabilized or stabilized ylides this results in E-alkene product.
References
No references
Wolff-Kishner reduction
Description
The Wolff-Kishner reaction is a selective carbonyl hydrogenation leaving unsaturations and esters intact. The originally method involved heating an aldehyde or a ketone with hydrazine (H2NNH2) and sodium or potassium hydroxide in a high-boiling alcohol such as triethylene glycol converts the carbonyl to a CH2 group. This reaction is an extension of imine formation, because hydrazone is an intermediate in the reaction. The Wolff-Kishner reduction is complementary to the Clemmensen reduction, base-labile molecules should be reduced by the Clemmensen method.
References
No references
Wurtz reaction
Description
The coupling of alkyl halides upon treatment with a metal, e.g. elemental sodium, to yield symmetrical alkanes, is called the Wurtz reaction.
References
New trends in green chemistry, V.K. Ahluwalia, M. Kidwai, 2004, pg.no.132;
Organic chemistry, Bhupinder mehta, Manju mehta, 2005, pg. no.146;
Organic Chemistry, Dr. R.K Gupta & R. K. Amit, pg. No: 371
Organic reactions: Mechanisms with problems, Rajpal Tyagi, 2005, pg. no.493.
Organic Syntheses, Coll. Vol. 1, p.228 (1941); Vol. 9, p.54 (1929).
Organic Syntheses, Coll. Vol. 6, p.133 (1988); Vol. 51, p.55 (1971).
alpha-Bromination of oxocompounds
Description
Alpha halogenation of aldehydes or ketones is an electrophil substitution reaction which can be either acid or base catalyzed and goes via the enol form of the aldehyde or ketone.
References
No references
alpha-Chlorination of oxocompounds
Description
Alpha halogenation of aldehydes or ketones is an electrophil substitution reaction which can be either acid or base catalyzed and goes via the enol form of the aldehyde or ketone.
References
No references
alpha-Hydroxynitrile formation
Description
This reaction is a nucleophilic addition of cyanide anion or a nitrile to an aldehyde or ketone followed by protonation of cyanide ion. Usually the cyanide source is potassium cyanide, sodium cyanide or trimethylsilyl cyanide. This nucleophilic addition is an equilibrium reaction, but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products. Aqueous base usually decomposes cyanohydrins completely. The reaction with sterically hindered ketones, or ketones like ArCOR or ArCOAr give poor yields. In that case ketones can be converted to cyanohydrins by treatment with diethylaluminum cyanide or with trimethylsilanecarbonitrile (Me3SiCN) in the presence of a Lewis acid or base. With aromatic aldehydes the benzoin condensation competes. With alpha,beta-unsaturated aldehydes and ketones, 1,4-addition competes.
References
No references
alpha-Iodination of oxocompounds
Description
Alpha halogenation of aldehydes or ketones is an electrophil substitution reaction which can be either acid or base catalyzed and goes via the enol form of the aldehyde or ketone.
References
No references
cross-Cannizzaro reaction
Description
Aldehydes that have no alpha-hydrogen give the Cannizzaro reaction upon treatment with a strong base, e.g. an alkali hydroxide. In this disproportionation reaction one molecule is reduced to the corresponding alcohol, while a second one is oxidized to the carboxylic acid. The synthetic importance of the reaction is limited, because as a consequence of the disproportionation, the yield of the alcohol as well as the carboxylic acid is restricted to 50%. However good yields of alcohols can often be obtained when the reaction is carried out in the presence of equimolar amounts of formaldehyde. The formaldehyde is oxidized to formic acid and concomitantly reduces the other aldehyde to the desired alcohol. This variant is called the crossed Cannizzaro reaction. With aldehydes that do have alpha-hydrogens, the aldol reaction takes place preferentially.
References
No references
von Braun degradation of tertiary amines
Description
Rosenmund von Braun degradation of tertiary amines cleaved by cyanogene bromide yields disubstituted cyanamide and alkyl halide. The reaction involves two nucleophilic substitutions via N-cyanoammonium bromide as intermediate. The first nucleophile is the tertiary amine, the second is the liberated bromide. Cyanide anion is not a nucleophile for aromatic systems, von Braun reaction is an exception.
References
No references

Base-catalyzed synthesis of substituted 1,2,4-triazoles can be performed by the condensation of a nitrile and a hydrazide.
References
Tetrahedron Letters, 2005, 46(19), 3429-3432.
2+2*1+1 Imidazole synthesis

Synthesis of imidazoles from 1,2-diketones via cyclocondensation with ammonia and aldehydes to form imidazole derivatives.
References
Organic Letters, 2004, 6(9), 1453-1456.
2,3-Dihydro-1H-benzimidazole synthesis

The acid-catalyzed condensation reactions of o-phenylenediamines with appropriate carbonyl compounds (aldehyde or ketone) afford dihydrobenzimidazoles.
References
Synthetic Communications, 1983, 13(12), 1033-1039.
3+2 Dihydroimidazole thione synthesis

Condensation of alpha-aminocarbonyl compound with various isothiocyanates or a thiocyanate salt (i.e. KSCN) leads to the N-substituted cyclic thioureas through the acyclic thiourea intermediates.
References
Bioorganic & Medicinal Chemistry, 2005, 13(13), 4209-4220.
3+2 Furan synthesis

This is a furan synthesis by 3+2 ring closure reaction. It can be assumed that the reaction proceeded through a preliminary Knoevenagel condensation between alpha-haloketone and beta-ketoester followed by condensation to provide furan derivatives.
References
Journal of the American Chemical Society, 1951, 73, 356-358.
3+2 Pyrazole synthesis

Condensation of hydrazines/hydrazides and 1,3-dicarbonyl compounds with acid leads to pyrazoles or substituted pyrazoles. Hydrazines/hydrazides reacted efficiently with various beta-diketones to afford the desired pyrazoles in good to excellent yields. The reactions between hydrazines/hydrazides and symmetrical beta-diketones gave single components; when an unsymmetrical beta-diketone is employed to react with hydrazines or hydrazides, two regioisomers can be formed.
References
Bioorganic & Medicinal Chemistry Letters, 2009, 19(17), 4963-4966.
Acylation of amine

Acylation of amines is an important method for protection of their basic functionality. Amines can react with a carboxylic acids or their derivatives and the reaction goes via tetrahedral intermediate. The acylating agents can be carboxylic acids, acid halides, esters, anhydrides, thiol acids and other acid derivatives.
References
No references
Acylation of nucleophiles with acid chlorides

Nucleophilic acyl substitution of amines, alcohols and thiols with acyl chlorides.
References
Synthetic Communications, 2002, 32, 23–30.
Acylation of nucleophiles with carboxylic acids

Nucleophilic acyl substitution of carboxylic acids with amines, alcohols or thiols to form amide, ester or thioester synthesis. The acid catalysed protonation provides extremly powerful electrophiles to form tetrahedral intermediate with nucleophiles. Carboxylic acid do not undergo substitution reaction under basic conditions, deprotonation of the acid gives the carboxylate salt.
References
No references
Addition of alcohols to alkynes

The addition of alcohols to alkynes proceeds to give the corresponding enol ethers.
References
Catalytic Heterofunctionalization, Antonio Togni, Hansjorg Grutzmacher, 2001, pg.no: 204-205.
Tetrahedron, 2006, 62, 2231-2234.
Tetrahedron Letters 50 (2009) 570–573.
Addition of hydrogen cyanide to alkynes

Addition of hydrogen cyanide to alkynes yields alkenyl cyanide.
References
Modern Organonickel Chemistry, Yoshinao Tamaru, 2005, pg.no: 111;
Principles of Organic Chemistry, Peter R. S. Murray, 1977, pg.no: 118.
J Chem Soc, Chemical Communications, 1982, 21, 1231-1232.
Aldol reaction

The enolate of an aldehyde or a ketone reacts at the α-carbon with the carbonyl of another molecule aldehyde or ketone under basic or acidic conditions to obtain β-hydroxy aldehyde or ketone. Base-catalysed aldol reactions may give the aldol product, or may give the dehydrated enone or enal by an E1cB mechanism. Acid-catalysed aldol reactions may give the aldol product, but usually give the dehydrated enone or enal by an E1 mechanism. In the case of cross condensation (occur between two different carbonyl compounds) one partner only must be capable of enolization, the other partner must be incapable of enolization and be more electrophilic than the enolizable partner.
References
No references
Alkyl Lithium formation from alkyl halides

Alkyl halide reacts with lithium metal to form alkyl lithium.
References
Organic chemistry, Marye Anne Fox, James K. Whitesell, 1997, pg. no.532;
Organic chemistry: an intermediate text, Robert V. Hoffman, 2004, pg. no.224;
Organolithiums: selectivity for synthesis, Jonathan Clayden, 2002, pg. no.152;
Invitation to organic chemistry, A William Johnson, 1999, pg. no.106.
Alkylation of amines with alkyl halides

This reaction is a nucleophilic attack of alkyl halides by primary or secondary amines, which usually gives a mixture of secondary and tertiary amines. Aryl halides are much less reactive than alkyl halides in the nucleophilic substitution reactions.
References
No references
Alkylation of phenols with benzyl chloride

Preparation of benzyl-phenyl ethers with benzyl chloride in the presence of potassium carbonate.
References
Resorcinol: chemistry, technology, and applications, Raj B. Durairaj, 2005, pg. no.48;
Comprehensive organic functional group transformations: synthesis: carbon, Alan R Katrizsky, Steven V.Ley, Otto Meth-Cohn, Charles W. Ress, FRS, 1995, pg. no.683;
Current medicinal chemistry, May 1994, pg. no.93;
Handbook of hydroxyacetophenones: preparation and physical properties, Volume 1, Robert Martin, 2005, pg. no.362.
Tetrahedron Letters, 2008, 49, 5039-5042.
Allylic halogenation of alkenes

Alkenes undergo allylic halogenation via free radical mechanism.
References
Organic Chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 216, 217;
Organic Chemistry, Solomons & Fryhle, 2006, pg.no: 695;
Christopher J. Easton, Alison J. Edwards, Stephen B. McNabb, Martin C. Merrett, Jenny L. O'Connell, Gregory W. Simpson, Jamie S. Simpson and Anthony C. Willis, Org. Biomol. Chem., 2003, 1, 2492 - 2498.
Alpha halogenation of carboxylic acids

Carbonyl compounds can be halogenated in the alpha position by halogens in acidic or basic solutions. The acid catalyzed enol formation is followed by the electrophilic attack of the halogen. In the case of the base catalysed reaction enolate is formed first followed by the halogenation, that usually won’t stop at the introduction of one halogen atom.
References
Synthetic Communication, 2004, 34, 889–893.
Arylation of amines

This is a nucleophilic substitution (SNAr) reaction, which requires catalyst to initiate the reaction.
References
No references
Baylis-Hillman vinyl alkylation

Amine catalyzed conversion of activated (electron-poor) alkenes to alpha-hydroxyalkyl olefines with carbonyl compounds.
References
Baylis, A.B., Hillman, M.E.D. Ger. Pat. 2155113, C.A., 1972, 77, 3417;
Baylis, A.B., Hillman, M.E.D, U.S. pat. 3743669 (1972, 1973);
Basavaiah D., Tetrahedron Lett., 1986, 27, 2031;
Basavaiah D., Tetrahedron Lett., 1987, 28, 4591, 4351;
Basavaiah D., Tetrahedron Lett., 1990, 31, 1621;
Drewes, S.E., Roos, G.H.P., Tetrahedron, 1988, 44, 4653;
Tetrahedron Lett., 2002, 43, 25, 4499;
K.-S. Park, J. Kim, H. Choo, Y. Chong, Synlett, 2007, Pg. no 395-398;
J. Cai, Z. Zhou, G. Zhao, C. Tang, Org. Lett., 2002, 4, 4723-4725;
H. Ito, Y. Takenaka, S. Fukunishi, K. Iguchi, Synthesis, 2005, 3035-3038;
C. Yu, L. Hu, J. Org. Chem., 2002, 67, 219-223;
K. Matsui, S. Takizawa, H. Sasai, Synlett, 2006, pg.no: 761-765.
Organic Letter, 2002, 4, 4723-4725.
Benzidine rearrangement

Benzidine rearrangement is an acid-catalyzed intramolecular rearrangement of aromatic hydrazocompounds. The name of the rearrangement has been derived from the major product; benzidine (4, 4'- diaminodiphenyl hydrazine), which is formed when hydrazobenzene is warmed with dil HCl or H2SO4.
References
Organic Reactions, Rajpal Tyagi, 2005, Pg. no: 43;
Synthesis of biaryls, Ivica Cepanec, 2004, Pg. no: 275, 276;
A. Burawoy, C. E. Vellins Journal of the Chemical Society 1954, 90;
H. R. Snyder, C. Weaver, C. D. Marshall, Journal of the American Chemical Society 1949, 7l, 289;
M. Nojima, T. Ando, N. Tokura, Journal of the Chemical Society, Perkin Transaction I 1976, 14, 1504;
Name reactions and reagents In Organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, 2005, Pg. no: 85;
Organic Letters, 2006, 8, 2047-2050.
March's Advanved Organic Chmistry, 5th Edition, 2001: The Benzidine Rearrangement
Benzimidazole synthesis

A traditional method for synthesis of benzimidazoles is the reaction between phenylenediamine and carboxylic acid under harsh dehydrating reaction conditions, for example, in the presence of HCl, polyphosphoric acid, H3BO3, or p-toluenesulfonic acid.
References
Organic Process Research & Development, 2010, 14(1), 215-224.
Benzothiazole synthesis

The reaction of 2-aminothiophenol and aryl aldehyde providing 2-aryl benzothiazole derivatives. Aliphatic aldehydes show poor yields of the desired products. This condensation–oxidation procedure is fairly general, and several functionalities, including hydroxyl and conjugated carbon–carbon double bonds, are tolerated.
References
Synthetic Communications, 2010, 40, 206-212.
Benzoxazole synthesis

The reaction of 2-aminothiophenol and aryl aldehyde providing 2-aryl benzothiazole derivatives. Aliphatic aldehydes show poor yields of the desired products. This condensation–oxidation procedure is fairly general, and several functionalities, including hydroxyl and conjugated carbon–carbon double bonds, are tolerated.
References
Angewandte Chemie, International Edition, 2008, 47, 9330-9333.
Beta HX elimination (Zaitsev elimination)

Alkyl halides typically undergo beta elimination reaction when heated with strong bases, hydroxides and alkoxides, to generate alkenes. The reaction involves loss of H and a halogen atom from adjacent carbons. The major reaction product is the alkene with more highly substituted (more stable) double bond.
References
Organic reaction mechanisms, V. K. Ahluwalia, Rakesh Kumar Parashar, 2002, pg. no. 58;
Organic chemistry (Sie), Carey, 2008, pg. no. 205, 206, 207, 339.
J Org Chem, 1970, 35, 1335-1338;
J Org Chem 1982,47,1944-1948;
Acc Chem Res, 1975, 8, 239-245;
Acc Chem Res, 1979, 12, 198-203;
March's Advanced Organic Chemistry, 5th ed., 2001.
Birch reduction

The reduction of aromatic compounds by alkali metals in liquid ammonia in the presence of an alcohol is called the Birch reduction, and yields selectively the 1,4-hydrogenated product.
References
Hydrocarbon chemistry, Arpad Molnar, 2003, Pg. no: 648.
Organic Reactions, Rajpal Tyagi, 2005, Pg. no: 71.
Synthetic approaches in organic chemistry, Raj K. Bansal, 1996, Pg. no: 114, 115,117;
Comprehensive Organic Synthesis, Barry M. Trost, Ian Fleming, 1992, Pg. no: 496.ű
Chem. Commun., 1999, 1263–1271
J Am Chem Soc, 1990, 112, 1280-1281
J Am Chem Soc, 1993, 115, 2205-2216
Bromination of aliphatic nitro compounds

Primary and secondary nitro compounds on treatment with Br2 in alkaline medium undergo bromination at alpha position.
References
Patent number: US 2632776, Mar. 24, 1953;
Organic Chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no.759;
Patent number: US 5180859, Jan. 19, 1993
J Org Chem, 1977, 42, 3764-3765.
Carboxylic acid addition to alkynes (Markovnikov)

Markovnikov addition of carboxylic acid to terminal alkyne produce enol ester.
References
Ruthenium in Organic Synthesis, Shun-Ichi Murahashi, 2004, pg.no: 197;
Immobilized catalysts: solid phases, immobilization and applications, Andreas Kirschning, 2004, page no. 125.
H. Doucet, B. Martin-Vaca, C. Bruneau, P.H. Dixneuf, J Org Chem, 60:7247-7255(1995);
L.J. Goossen, J. Paetzold, D. Koley, ChemComm, 706-707(2003);
J. Tripathy, M. Bhattacharjee, Tetrahedron Letters, 50:4863-4865(2009);
Tetrahedron Letters, 2002, 43, 9259-9263.
Carboxylic acid addition to alkynes (anti-Markovnikov)

Anti-Markovnikov addition of carboxylic acid to alkyne yields enol ester.
References
Advanced Organic Chemistry,Francis A. Carey,2001, pg.no: 373;
P.E. Peterson and J.E. Dudley, J. Am. Chem. Soc, 88:4990 (1966);
R.H. Summearville, C.A. Senkler, P.V.R. Schleyer, J. Am. Chem. Soc, 96:1100 (1974);
Metal Vinylidenes and Allenylidenes in Catalysis, Christian Bruneau, Pierre Dixneuf, 2008, pg.no: 316;
Ruthenium Catalysts and Fine Chemistry, Christian Bruneau, Pierre H. Dixneuf, 2004, pg.no:130.
L.J. Goossen, J. Paetzold, D. Koley, Chem. Comm., 706-707(2003);
J. Tripathy, M. Bhattacharjee, Tetrahedron Letters, 50:4863-4865(2009);
H. Doucet, B. Martin-Vaca, C. Bruneau, P.H. Dixneuf, J. Org. Chem., 60:7247-7255(1995);
Catalytic hydration of alkenes

Alkenes undergo catalytic hydration to form carbonyl compounds.
References
Transition metal reagents and catalysts, Jiro Tsuji, 2002, pg.no: 421, 422;
Advanced Organic Chemistry: Part B: Reactions and Synthesis, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 710, 711.
Organic Synthesis, 1990, 7, 137.
Catalytic hydrogenation of aromatic compounds with Rh_C or Pt_C

Catalytic hydrogenation of aromatic compounds in presence of catalytic amounts of Rh/C or Pt/C to form hydrogenated cyclic compounds.
References
Heterogeneous catalysis for the synthetic chemist, Robert L. Augustine, 1996, pg. no.408, 416;
Green chemistry and catalysis, Roger A. Sheldon, Isabel Arends, Ulf Hanefeld, 2007, pg. no.98;
Introduction to organic chemistry II, Seth Robert Elsheimer, 2000, pg. no.12;
Hydrocarbon chemistry, George Andrew Olah, Arpad Molnar, 1995, pg. no.632;
Comprehensive organic synthesis: selectivity, strategy, and efficiency, Barry M. Trost, Ian Fleming, 1991, pg. no.438.
Journal of Organometallic Chemistry, 2004, 689, 639–646.
Angew. Chem. Int. Ed., 2007, 46, 1152 –1155.
Catalytic hydrogenation of aromatic hydrocarbons with H2/Ni or H2/Pd-C

Catalytic hydrogenation of aromatic hydrocarbons to alicylic compounds.
References
University Chemistry, Vol. I By C. Parameshwara Murthy, 2008, Page. no:408;
Aromatic chemistry, John D. Hepworth, David R. Waring, Michael J. Waring, 2002, Pg. no: 129;
Modern organonickel chemistry, Yoshinao Tamaru, 2005, Pg. no: 279;
Patent, EP2141167A1, 2010.
Some modern methods of organic synthesis By W. Carruthers, Edition:2 -1971, Page No. 310;
Comprehensive organic synthesis: selectivity, strategy & Efficiency in Modern Organic chemistry, Vol 8, Barry M. Trost, Ian Fleming, 1991, Pg. no: 438;
Heterogeneous catalysis for the synthetic chemist, Robert L. Augustine, 1996, Pg. no: 403 & 418.
Catalytic hydrogenation of phenols

Selective hydrogenation of phenol to cyclohexanones takes place under a variety of conditions and over different catalysts.
References
1. Industrial organic chemicals, Part 2, Harold Wittcoff, B. G. Reuben, Jeffrey S. Plotkin, 2004, pg. no.283;
2. High pressure chemistry: synthetic, mechanistic, and supercritical applications, Rudi Van Eldik, Frank-Gerrit Klarner, 2002, pg. no.386;
3. Some modern methods of organic synthesis, W. Carruthers, 2004, pg. no.419;
4. Heterogeneous catalysis for the synthetic chemist, Robert L. Augustine, 1996, pg. no.412.
5. US patent 3965187
Chan reduction of acetylenes

Stereoselective reduction of propargyl alcohols to E-allylic alcohols by means of sodium bis(2-methoxyethoxy)aluminium hydride (SMEAH or Red-Al) or LiAlH4.
References
Ka-Kong Chan, J. Org. Chem. 1976, 41, 62;
Ka-Kong Chan, N. Cohen, J.P. De Noble, A.C. Specian, Jr. G. Saucy, J. Org. Chem. 1976, 41, 3497;
Ka-Kong Chan, J. Org. Chem. 1978, 43, 3435;
N.M. Irvine, Phytochemistry, 2000, 53, 349-355;
E.J. Corey, J.A. Katzenellenboger, G.H. Posner, J. Am.Chem. Soc. 1967, 89, 4245-4247;
S.E. Denmark, T.K. Jones, J. Org. Chem. 1982, 47, 4595-4597;
J.A. Marshall, B.S. DeHoff, J. Org. Chem. 1986, 51, 863-872;
D.J. Kucera, S.J. O'Connor, L.E. Overman, J. Org. Chem. 1993, 58, 5304-5306;
E. Roulland, C. Monneret, J.-C. Florent, J. Org. Chem. 2002, 67, 4399-4406;
C.T. Meta, K. Koide, Org. Lett. 2004, 11, 6, 1785-1787;
Organic synthesis based on name reactions, A. Hassner and C.stumper, 2002, pg.no: 56;
Name reactions by Jie Jack Li, 2006, pg.no: 114;
Midland, M. M. Gabriel, J. J. Org. Chem. 1985, 50, 1143;
Meta. C.T. Koide, K. Org. Lett.2004, 6, 1785;
Name reactions and reagents in Organic synthesis, 2nd Edition, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, Jr., pg.no: 139;
E. B. Bates, E. R. H. Jones, M. C. Whiting, Journal of the Chemical Society, 1954, 1854;
T. Eguchi, T. Koudate, K. Kakinuma, Tetrahedron, 1993,49,4527;
C. Agami, M. Cases, F. Couty, Journal of Organic Chemistry, 1994,59,1931.
Organic Letters, 2004, 6, 4073-4076.
Journal of Organic Chemistry, 1995, 60, 6046-6056.
Cleavage of acyclic ethers with HI (SN1 mechanism)

Tertiary ethers undergoes cleavage with HI by an SN1 mechanism to form an alcohol and an alkyliodide. Cleavage of the C-O bond then occurs in two steps, the bond to the leaving group is broken to form a carbocation, and then the bond to the nucleophile is formed. This generates alkyl iodide.
References
Organic chemistry (Sie) 2E, 2008, pg. no.345;
Chem 4113 Organic chemistry II, Lecture notes, chapter 18.
J. Org. Chem. 2000, 65, 7740-7746.
Cleavage of acyclic ethers with HI (SN1 mechanism)

Tertiary ethers undergoes cleavage with HI by an SN1 mechanism to form an alcohol and an alkyliodide. Cleavage of the C-O bond then occurs in two steps, the bond to the leaving group is broken to form a carbocation, and then the bond to the nucleophile is formed. This generates alkyl iodide.
References
Organic chemistry (Sie) 2E, 2008, pg. no.345;
Chem 4113 Organic chemistry II, Lecture notes, chapter 18.
J. Org. Chem. 2000, 65, 7740-7746.
Cleavage of epoxides

Hydrolysis of epoxides leading to diols via carbocation rearrangement (mechanism analogous to SN1 and SN2 operate under neutral and acid catalyzed conditions).
References
Synthesis, 17, 2005, 2897-2900;
J. Org. Chem., 2008, 73, 2270-2274;
Advanced organic chemistry: structure and mechanisms, Francis A. Carey, Richard J. Sundberg, 2001, pg. no.513;
Catalytic oxidations with hydrogen peroxide as oxidant, Giorgio Strukul, 1992, pg. no.28.
Cleavage of ethers with HI (SN2 mechanism)

Primary and secondary ethers are cleaved by strong acids such as hydroiodic acid (or HBr) in a nucleophilic substitution (SN2) reaction to form an alcohol and an alkyliodide.
References
The Last American Frontier, Frederic L. Paxson, 2001, pg. no.299;
Organic Chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, pg. no. 427;
Organic Chemistry: Aromatic, Alcohols Aldehydes & Acids, Amit Arora, pg. no. 103;
Organic Chemistry, J. William Suggs, pg. no. 255;
Organic chemistry, Dhawan, 2007, pg. no.7-9.
J. Org. Chem. 2000, 65, 7740-7746.
Cleavage of vinyl ethers

Acid-catalyzed cleavage of the vinyl ethers to give alcohols and carbonyl compounds (aldehyde or ketone).
References
Hydrolysis of vinyl ethers, US Patent 2533172, 1950;
Organic chemistry, Thomas N. Sorrell, 2006, pg.no.638;
Can. J. Chem. Vol. 65. 1987
Journal of Organometallic Chemistry 692 (2007) 472–480;
Clemmensen reduction

Clemmensen reaction is a reduction of carbonyl functional group of aldehydes or ketones. It employs zinc metal dissolving in concentrated hydrochloric acid; this reaction is really reasonable only for compounds with just the one functional group. The Clemmensen reduction is complementary to the Wolff-Kishner reduction, which is run under strongly basic conditions. Acid-labile molecules should be reduced by the Wolff-Kishner protocol.
References
No references
Condensation reaction of primary amines and oxocompounds

Nucleophilic addition-elimination reaction, addition of ammonia or primary amines type RNH2 or ArNH2 to aldehydes and ketones results in carbinolamine which undergoes dehydration to form the corresponding imine and a molecule of water. (A number of compounds of the general type H2NZ react with aldehydes and ketones in a manner analogous to that of primary amines).
References
No references
Condensation reaction of secondary amines and oxocompounds

In the first step nucleophilic attack of amine to the carbonyl group results in carbinolamine which undergoes dehydration to yield an alkenyl-substituted amine, or enamine and a molecule of water. In general, ketones react more slowly and longer reaction times are often required. Enamine and imine are tautomers, enamines are normally stable when there is no hydrogen on the nitrogen.
References
No references
Corey-Chaykovsky reaction

Corey-Chaykovsky reaction entails the reaction of sulfur ylide, either dimethylsulfoxonium methylide (Corey's ylide, sometimes known as DMSY) or dimethylsulfonium methylide, with electrophile, such as carbonyl, olefin, imine, or tiocarbonyl, to offer the corresponding epoxide, cyclopropane, aziridine, or thiirane.
References
Corey, E.J., J. Am. Chem. Coc., 1962, 84, 866;
Kuhn, R., Angew. Chem., 1957, 68, 570;
Kuhn, R., Liebigs Ann., 1958, 611, 117;
Olah, G.A., Synthesis, 1990, 887;
Name Reactions in Heterocyclic Chemistry, Jie Jack Li, 2004, pg.no: 2;
Name Reactions, Jie Jack Li, 2006, pg.no: 157,158;
R. J. Paxton, R. J. K. Taylor, Synlett, 2007, 633-637;
S. Chandrasekhar, Ch. Narasihmulu, V. Jagadeshwar, K. Venkatram Reddy, Tetrahedron Lett., 2003, 44, 3629-3630.
J. AM. CHEM. SOC. 2008, 130, 10078–10079
Dehalogenation of vicinal dihalides

Elimination of dihalogens from vicinal dihalides resulting in the formation of olefins.
References
Organic Chemistry By Marye Anne Fox, James K. Whitesell, pg. no. 443;
Organic Chemistry (Sie), Pine, pg. no. 488, 489;
A textbook of organic chemistry, August Bernthsen, Raj K. Bansal, 2003, pg. no. 183;
Comprehensive Chemistry XI, pg. no. 1112.
Journal of Organic Chemistry, 2005, 70, 8621-8624.
Tetrahedron, 1998, 54, 1021-1028.
Reduction in organic chemistry, M. Hudlicky 1984 (Wiley-New York).
Dehydration of alcohols to alkenes

Heating an alcohol with a catalytic amount of a strong acid (usually sulfuric acid or phosphoric acid) results in the formation of an alkene, with water as a byproduct. These dehydration reactions typically follow E1 mechanism.
References
Introduction to general, organic, and biochemistry, Frederick A. Bettelheim, William H. Brown, Mary K. Campbell,2009, pg. no. 379;
Organic Chemistry (sie), Carey, 2008, pg. no.197, 198, 199, 202;
General, Organic, and Biological chemistry, Stephen Stocker, 2009, pg. no.377;
Organic chemistry, Dhawan, 2007, pg. no. 6.25.
J. Org. Chem. 1980, 45, 919-920;
J. Org. Chem. 1967, 32, 3386-3389;
J. Org. Chem. 1982,47, 900-902;
Diazotisation of primary anilines

Diazonium salt formation is a nitrosation reaction of primary aniline with nitrous acid which is formed in situ from sodium nitrite and strong acid such as HCl, H2SO4. In aqueous solution diazonium salts are unstable at temperatures above +5 °C. Aryl diazonium salts generally react with nucleophiles with loss of nitrogen. They are important intermediates in the formation of aryl halides (Sandmeyer and Schiemann reactions) and azo compounds.
References
No references
Diels-Alder cycloaddition

4+2 cyclic addition of dienophile and diene to form an adduct.
References
Synthetic Approaches in Organic Chemistry, Raj K. Bansal, 1998, pg.no: 311, 312;
O.Diels and K. Alder, Ann., 460, 98 (1928);
J.Sauer, Angew. Chem.Int. Ed. (Engl), 6, 16 (1967);
The Diels-Alder reaction, Francesco Fringuelli, Aldo Taticchi, 2002, pg.no: 29, 30, 32, 35, 46, 51.
Organic Letters, 2005, 7, 2539-2541.
AngewChem-2008-47-6634.
Diels-Alder reaction with fused aromatic hydrocarbons

Bachmann and Scott, J. Am. Chem. Soc, 1948, 70, 1458-61; Organic Reactions, Vol-IV, The Diels-Alder Reaction with Maleic Anhydride, Milton C Kloetzel, 1948, Pg. no: 11.
References
Chemistry under extreme or non-classical conditions, Rudi van Eldik, Colin D. Hubbard, 1996, Pg. no: 171;
Diels-Alder reaction between naphthalene and N-phenylmaleimide under ambient and high pressure conditions, Gulnara G. Iskhakova, Vladimir D. Kiselev, Elena A. Kashaeva, Lubov’ N. Potapova, Evgeny A. Berdnikov, Dmitry B. Krivolapov, and Igor A. Litvinov, 2005, Pg. no: 7;
Bachmann and Scott, J. Am. Chem. Soc, 1948, 70, 1458-61;
Organic Reactions, Vol-IV, The Diels-Alder Reaction with Maleic Anhydride, Milton C Kloetzel, 1948, Pg. no: 11, 30;
The Diels-Alder reaction, Francesco Fringuelli, Aldo Taticchi, 2002 , Pg. no: 196;
The Porphyrin Handbook, Volumes 11-20, Karl M. Kadish, Roger Guilard, Kevin M. Smith, 2003, Pg. no: 24;
Advanced Organic Chemistry, Francis A. Carey, Richard J. Sundberg, 2000, Pg. no: 859.
Org Lett, 2007, 7, 2859-2862.
Direct alkylation of amines with epoxide

This is a nucleophilic ring-opening reaction of epoxides by ammonia or amines.
References
No references
Doering-LaFlamme allene synthesis

Allene synthesis from alkenes via geminal dihalocyclopropanes. (two-step reaction)
References
W. v. Doering, A.K. Hoffmann, J. Am. Chem. Soc., 1954, 76, 6162;
P.M. La Flamme, Tetrahedron, 1958, 2, 75;
W.R. Moore, H.R. Ward, J. Org. Chem., 1960, 25, 2073;
W.R. Moore, J. Org. Chem., 1962, 27, 4182;
L. Skattebol, Tetrahedron Lett. 1961, 167;
E. Chinoporos, Chem. Rev., 1963, 63, 235;
T. Kitayama, T. Masuda, K. Sakai, C. Imada, Y. Yonekura, Y. Kawai, Tetrahedron, 2006, 62, 47, 10859-10864;
V. Franzen, Reaktionsmechanismen I (Heidelberg, 1958), p 14;
T. J. Logan, Tetrahedron Lett., 1961, 2, 173;
L. Skettebol, Acta Chem.Scand., 1963, 17,1683;
L.K. Sydnes, Chem. Rev., 2003, 103, 1133-1150;
J. Hine, Divalent Carbon (New York, 1964), p 20;
M. Murray, Houben-Weyl 1977, 5/2a, 985;
V. Nair, Comp. Org. Syn. 1991, 4, 1009-1012;
US 2933544 (1960);
Organic syntheses based on name reactions, Alfred Hassner, C. Stumer, pg.no: 91.
Ether formation from alcohols

Heating alcohol with concentrated sulfuric acid results in condensation of two molecules of alcohol with elimination of water molecule to form ether. The reaction is catalyzed by H+ ions to form oxonium ion that undergoes substitution (SN1 or SN2) by another molecule of alcohol to form ether.
References
Organic Chemistry (Sie), Carey, 2008, pg. no. 669;
The organic chemistry problem solver, Volume 2, Max Fogiel, Research and Education Association, 1994, pg. no. 588;
Organic chemistry demystified, D. R. Bloch, 2006, pg. no. 320;
Phenolic compound biochemistry, Wilfred Vermerris, Ralph Nicholson, 2006, pg. no. 47;
Comprehensive organic reactions in aqueous media, Chao-Jun Li, Tak-Hang Chan, 2007, pg. no. 135.
General, organic, and biological chemistry, H. Stephen Stoker, 2007, pg. no.378.
J. Org. Chem. 1996, 61, 324-328.
J. Am. Chem. Soc. 1999, 121, 10711-10718.
Fischer esterification

When carboxylic acids are treated with large excess of an alcohol in the presence of strong acid catalyst, esters are formed. The reaction is an equilibrium process but can be driven to favor the ester by removing the water that is formed. The most commonly used acid catalysts are Lewis acids, sulfuric acid, tosic acid; for sensitive substrate dicyclohexylcarbodiimide is often used.
References
No references
Formation of acetals and ketals

Acetals and ketals are formed by treatment of aldehydes and ketones with alcohols in the presence of acid catalysts. Lewis acids can be used in conjunction with alcohols. Acetals and ketals are quite stable to bases, therefore a useful method of protection of aldehyde or ketone functions from attack by bases.
References
No references
Formation of alkylated, alpha unsaturated nitro compound

A base catalyzed C-C bond forming reaction between nitro compound and aldehyde; further elimination of water to produce alkylated alpha unsaturated nitro compound (nitroalkene). It is a two step reaction which involves the following steps. 1. Nitroaldol reaction: Condensation reaction between a nitro compound and aldehyde. 2. Dehydration: By suitable functionalization of the hydroxy group followed by a base-induced elimination of water from the resulting derivative.
References
Org. Lett., 2008, 10, 1449-1451;
The nitro group in organic synthesis, Noboru Ono, 2001, pg. no. 41, 166.
Formation of cyclic acetals and ketals

The expected product of nucleophilic addition of the alcohol to the carbonyl group of aldehydes or ketones is called cyclic acetals or ketals. Cyclic acetals and ketals are often used to protect aldehydes and ketones, because acetals can be introduced and removed readily. The five- or six-membered 1,3-dioxanes and 1,3-dioxolans derived from ethylene glycol are the most commonly encountered examples.
References
No references
Friedel-Crafts acylation

Acylation of aromatic compounds by means of acyl halides in the presence of Lewis acids.
References
No references
Friedel-Crafts alkylation

The synthesis of an alkylated aromatic compound by reaction of an aromatic substrate with an alkyl halide, catalyzed by a Lewis acid, is called the Friedel–Crafts alkylation. The general principle is the intermediate formation of a carbenium ion species, which is capable of reacting as the electrophile in an electrophilic aromatic substitution reaction.
References
Hydrocarbon chemistry, Arpad Molnar, 2003, Pg. no: 229, 237, 233;
Instant notes organic chemistry, Graham L. Patrick, 2004, Pg. no: 142;
Advanced organic chemistry, Part 2, Francis A. Carey, Richard J. Sundberg, 2007, Pg. no: 1016;
Advanced organic chemistry, Francis A. Carey, Richard J. Sundberg, 2007, Pg. no: 583.
Organic Synthesis, 1943, 2, p. 243.
Fritsch-Buttenberg-Wiechell acetylene synthesis (rearrangement)

Alpha elimination from haloethylenes leading via carbene rearrangement to acetylenes.
References
Fritsch, P.Liebigs Ann, 1894, 279, 319;
Buttenberg, W.P.Liebigs Ann, 1894, 279, 327;
Wiechell, H.Liebigs Ann, 1894, 279, 332;
Acetylene Chemistry, François Diederich, Peter J. Stang, Rik R. Tykwinski, pg.no.262;
Curtin, D.Y.J. Am. Chem. Soc., 1958, 80, 4599;
Kobrich, G.Chem. Ber, 1972, 105, 1674;
Kobrich, G.Angew. Chem. Int. Ed., 1965, 449;
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Grignard compound addition to carbonyl compounds

Grignard reaction is the addition of an organomagnesium halide (Grignard reagent) to a ketone or aldehyde, to form a tertiary or secondary alcohol. The reaction with formaldehyde leads to a primary alcohol.
References
No references
Grignard reaction to carbonyl compounds

Synthesis of primer, sec. or tert. alcohols via addition of Grignard reagent to carbonyl compounds.
References
Grignard, V.Compt. Rend., 1900, 130, 1322;
Eicher, Patai, "The Chemistry of the Carbonyl Group" Interscience Publishers, New York, 1966, pp. 621-693;
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Grignard reagent formation

Synthesis of Grignard reagent from alkyl or aryl halides.
References
No references
Halogen addition to alkenes

Halogens react with alkenes by electrophilic addition to form vicinal dihalide.
References
Advanced Organic Chemistry, A. Carey, Richard J. Sundberg, 2000, pg.no: 200, 202;
Hydrocarbon Chemistry, A. Olah, Árpád Molnár, 2003, pg.no: 308;
J. H. Rolston and K. Yates. J. Am. Chem. Soc. 91:1469, (1969);
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OrgLett-2003-5-4501-4504.
Halogen addition to alkynes

Addition of one equivalent of halogen to alkyne results in formation of dihaloalkenes.
References
Chemistry Vol (1 & 2), AK Srivastava and PC Jain, pg.no: 1304;
Organic Chemistry, J. William Suggs, 2002, pg.no: 181;
Advanced Organic Chemistry, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 540.
Tetrahedron, 2001, 57, 7417-7422.
Organic Letters, 2001, 3, 1061-1063.
J Am Chem Soc, 1938, 60, 1711-1713.
Halogenation of alcohols with hydrogen halides

Nucleophilic substitution reaction of alcohols with hydrogen halides to generate an alkyl halide and water.
References
Principles of organic chemistry, By Peter R. S. Murray, 1977, pg. no.174;
Introduction to organic laboratory techniques: a small scale approach By Donald L. Pavia, 2005, pg. no.188;
Organic Chemistry (Sie), Carey, 2008, pg. no.148, 345.
Halogenation of alkanes (UV light)

No description
References
Organic Chemistry, Robert Thornton Morrison, Robert Neilson Boyd, 2000, pg.no: 105, 448;
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J. Org. Chem. 1997, 62, 236-237.
Eur. J. Org. Chem. 2006, 483–488
Halogenation of alkanes (substitution)

Substitution reaction of alkane to produce alkyl halide.
References
P. Kovacic, H.C. Volz, J. Am. Chem. Soc., 1959, 81, 3261;
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Halogenation of aromatic hydrocarbons

Halogenation of aromatic hydrocarbons takes place through electrophilic substitution to produce aryl halides.
References
Organic chemistry, Thomas N. Sorrell, 2006, Pg. no: 571;
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Tetrahedron Letters, 2010, 51, 340–342.
Hantzsch pyrrole synthesis

The Hantzsch pyrrole synthesis is an alkylation-cyclocondensation reaction involving a primary amine, a beta-ketoester or beta-ketoamide and an alpha-haloketone or aldehyde leading to tetra- or pentasubstituted pyrroles. The reaction can be performed either as a three component reaction or in a two component pathway by first treating a primary amine with a beta-ketoester or beta-ketoamide to obtain an enaminone followed by reaction with an alpha-bromoketone to afford the pyrrole ring.
References
Bioorganic and Medical Chemistry Letters, 1998, 8, 2381-2384.
Hantzsch thiazole synthesis

The cyclocondensation of alpha-halocarbonyl compounds with thioamides (Hantzsch synthesis) provide thiazoles. The Hantzsch synthesis involves three intermediate steps: the halogen atom of the alpha-halo aldehyde or alpha-halo ketone is nucleophilically substituted; the resulting S-alkyliminium salt undergoes a proton transfer; cyclization produces a salt which is converted into a 2,5-disubstituted thiazole in protic solvents by an acid-catalysed elimination of water. Thiazoles do not react as 1,3-dienes, i.e. they do not undergo a Diels-Alder reaction.
References
Tetrahedron, 2008, 64, 4384-4386.
Heck reaction (intermolecular)

The Heck reaction is a palladium catalyzed C-C coupling between aryl or vinyl halides or pseudohalides (eg. triflates, tosylates, thiomethyls) and activated alkenes in the presence of base. One of the benefits of the Heck reaction is its outstanding trans selectivity.
References
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Heck reaction (intramolecular)

Unhindered alkenes undergo intramolecular Heck reaction and forms C-C coupled compounds.
References
Transition Metal Reagents and Catalysts, Jiro Tsuji, 2002, pg.no: 45;
Palladium in heterocyclic chemistry, Jie Jack Li, Gordon W. Gribble,2000, pg.no: 56, 57;
Transition Metal Reagents and Catalysts, Jiro Tsuji, 2002, pg.no: 41,43;
Microwaves in Organic and Medicinal Chemistry, C. Oliver Kappe, Alexander Stadler, 2005, pg.no: 113.
J Am Chem Soc, 1996, 118, 12, 2843-2859.
Hinsberg thiophene synthesis

Hinsberg synthesis is a condensation reaction of alpha diketones and activated thioethers under basic conditions which provides 3,4-disubstituted-thiophene-2,5-dicarboxylic acids upon hydrolysis of the crude ester with aqueous acid. A notable utilization of the Hinsberg procedure was executed in the synthesis of a thiophene analogue of porphyrin.
References
Name Reactions in Heterocyclic Chemistry, Jie-Jack Li, 2005, p. 199-205.
Hofmann elimination

Hofmann degradation or beta-elimination reaction usually means the cleavage of quaternary ammonium hydroxide to form alkene and tertiary amine. In the first step primary, secondary, or tertiary amine is treated with enough methyl iodide to form quaternary ammonium iodide. In the second step, the iodide is converted to the hydroxide by treatment with silver oxide. The third step is the decomposition by pyrolysis. The beta-elimination takes place on the beta-carbon with the least branching (In contrast, E2 elimination of alkyl halides give predominance of the alkene with the greatest amount of branching at the double bond).
References
No references
Hofmann-Löffler-Freytag reaction

The synthesis of pyrrolidine or piperidine derivatives by thermal or photochemical decomposition of the protonated aliphatic N-haloamines is generally known as Hofmann–Löffler–Freytag reaction. Many experimental evidences support the radical mechanism of this reaction, such as the initiation of the reaction by either photo-irradiation or traditional radical initiators and the inhibition of reaction by oxygen. In this reaction, hydrogen abstraction is the chain-propagating step. This reaction has been applied for the preparation of substituted pyrrolidines and piperidines.
References
No references
Horner–Wadsworth–Emmons reaction

The so-called Wittig-Horner reaction is the reaction of aldehydes or ketones with stabilized phosphorus ylides (phosphonate carbanions) leads to olefins with excellent E-selectivity.
References
No references
Huisgen triazole synthesis

Huisgen 1,3-dipolar cycloaddition convenient and straightforward approach for the preparation of a wide range of five-membered ring heterocycles. The Cu(I)-catalyzed, stepwise cycloaddition of an alkyne dipolarophile with a azide as 1,3-dipolar compound exhibits broad scope and provides 1,4-disubstituted 1,2,3-triazoles in excellent yields and high regioselectivity.
References
Angewandte Chemie Int. Ed., 2002, 41, 2596-2599.
Hydration of alkenes

Alkenes can be hydrated quickly under mild conditions without rearrangement of the product. The regiochemistry of water addition to alkenes follows Markovnikov's rule to form alcohols.
References
Comprehensive Organic Reactions in Aqueous Media, Chao-Jun Li, Tak-Hang Chan, 2007, pg.no: 29;
Addition and Elimination Reactions of Aliphatic Compounds, C. H. Bamford, Charles, 1973, pg.no: 300.
Tetrahedron, 2005, 61, 11986-11990;
J. Org. Chem. 2002, 67, 3202-3212;
Hydration of alkynes (Markovnikov's addition)

Alkynes undergo acid-catalyzed Markovnikov addition of water to give enols that immediately tautomerise to form ketones. In generaly, H+, Hg, Pd, Pt, Au... catalysts are used to the form the Markovnikov product and Ru catalyst is used to form the anti-Markovnikov product.
References
Advanced Organic Chemistry, Francis A.CArey, Richard J. Sundberg, 2001, pg.no: 225;
R. W .Bott, C. Eaborn, and D. R. M.Walton, J.Chem. Soc.1965:384;
G.N. Stacy and R.A. Mikulec, Org. Synth. IV: 13 (1963);
W. G. Dauben and D.J. Hart, J. Org. Chem. 42:3789(1977);
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Hydrocarbon chemistry, George Andrew Olah, Arpad Molnar, pg.no: 287;
Organic Chemistry (Sie) Carey, pg.no: 371.
Journal of American Chemical Society, 2003, 125, 11925-11935.
Hydration of terminal alkynes (anti-Markovnikov's addition)

The anti-Markovnikov hydration of terminal alkynes to give aldehydes, catalyzed by Ruthenium complexes. In generaly, H+, Hg, Pd, Pt, Au... catalysts are used to the form the Markovnikov product and Ru catalyst is used to form the anti-Markovnikov product.
References
Ruthenium in Organic Synthesis, Shun-lchi Murahashi, 2004, pg.no: 190, 192;
Ruthenium Catalysts and Fine Chemistry, Christian Bruneau, Pierre H. Dixneuf, 2004, pg.no: 132.
Makoto Tokunaga and Yasuo Wakatsuki, AngewChem, 1998, 37, 2867-2869.;
Douglas B. Grotjahn and Daniel A. Lev, JACS, 2004, 126, 12232-12233.;
Aure´lie Labonne, Thomas Kribber, and Lukas Hintermann, OrgLett, 2006, 8, 5853-5856.;
Toshiaki Suzuki, Makoto Tokunaga and Yasuo Wakatsuki, OrgLett, 2001, 3, 735-737.;
J. Am. Chem. Soc. 2004, 126, 12232-12233.
Org Lett, 2006, 8, 5853-5856.
Angew. Chem. Int. Ed. 1998, 37, 2867-2869.
Organic Chemistry, F.A. Carey, 4th Edition, 2000.
Hydrogen bromide addition to alkenes (anti-Markovnikov)

Free-radical addition reaction of alkene with hydrogen bromide to produce alkyl bromide. Peroxides facilitate the formation of a bromine radical and the regioselectivity is anti-Markovnikov.
References
Advanced organic chemistry, Part A, Francis A Carey and Richard J.Sundberg, 2001, Pg.no: 708, 710, 711;
W. J. Bailey and S.S. Hirsch, J. Org. Chem. 28:2894 (1963);
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H. L. Goering and L. L. Sims, J. Am. Chem, Soc. 77:3465 (1955);
N.A. LeBel, R. F. Czaja, and A. DeBoer, J. Org. Chem. 34:3112 (1969);
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H. L. Goering, P. I. Abell, and B. F. Aycock, J. Am. Chem. Soc. 74:3588 (1952).
J. March, Advanced Organic Chemistry, 5th Edition, 2001.
Organic Syntheses, Coll. Vol. 7, p.59 (1990); Vol. 62, p.140 (1984)
Hydrogen halide addition to alkenes (Markovnikov)

Alkenes undergo electrophilic addition reaction with hydrogen halide to produce alkyl halide.
References
Advanced Organic Chemistry, Part A, Francis A Carey and Richard J.Sundberg, 2001, pg.no: 352, 355, 356, 357;
Advanced Organic Chemistry, Part B, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 291;
Y. Pocker and K. D. Stevens, J. Am. Chem, Soc. 91, 4205 (1969);
S. H. Kang, W. J. Kim and Y. B. Chae, Tetrahedron Lett., 1988, 29, 5169;
Comprehensive organic synthesis, Barry M. Trost, Ian Fleming, Martin F. Semmelhack, 1991, Vol 4, pg.no: 279.
J. March, Advanced Organic Chemistry, 5th Edition, 2001.
Hydrogen halide addition to alkynes

Hydrogen chloride, hydrogen bromide, hydrogen iodide add to alkyne yielding alkenyl halide.
References
Organic Chemistry, Raj K Bansal, pg.no: 228;
Advanced Organic Chemistry, Francis A Cary,Richard J. Sundberg, 2007, pg.no: 335;
Hydrocarbon Chemistry, Arpad Molnar, 2003, pg.no: 297;
Unified Course in Chemistry, O.P Agarwal, pg.no: 389.
J. Org. Chem., 1994, 59, 3102-3112.
Hydrolytic carbon monoxide addition to alkynes

Hydrocarboxylation of alkynes to form carboxylic acids in presence of nickel catalyzed compounds.
References
Carbonylation: Direct Synthesis of Carbonyl Compounds, H. M. Colquhoun, D. J. Thompson, M. V. Twigg, 1991, pg. no: 107;
Modern Organo nickel Chemistry, Yoshinao Tamaru, 2006, pg. no: 233;
Comprehensive Organic Reactions in Aqueous Media, Chao-Jun Li, Tak-Hang Chan, 2007, pg.no: 108.
US Patent, 1958, 2-845-451.
Hydroxyation of alkenes with potassium permanganate

Alkenes on treatment with alkaline potassium permanganate at room temperature yields cis-1,2-diols.
References
Organic chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 211;
Invitation to Organic Chemistry, A. William Johnson, 1998, pg.no: 205;
Organic reaction mechanisms, V.K.Ahluwalia, R.K.Parashar, 2003, pg.no: 140;
Organic Reaction Mechanisms, Bansal, 1998, pg.no: 588;
Organic synthetic methods, JamesRoyal Hanson, 2002, pg.no: 100.
Organic Synthesis, 1941, 2, 307.
Hydroxymethylation of phenols

The reaction of phenol with formaldehyde in the presence of alkaline medium results in hydroxymethylation of phenol at ortho and para positions. The reaction is known as Lederer Manasse reaction.
References
Fine chemicals through heterogenous catalysis, Roger A. Sheldon, Herman van Bekkum, 2001, pg. no.175, 176;
Advanced organic chemistry: Structure and mechanisms, Francis A. Carey, Richard J. Sundberg, 2007, pg. no.827;
Adhesion 9, K. W. Allen, 1984, pg. no.5;
Calixarenes: an introduction, Carl David Gutshe, 2008, pg. no.12.
J. Chem. Research (S), 2003, 200-203.
Intramolecular amine alkylation

The intramolecular alkylation of amines yield cyclic amines, usually aziridines, pyrrolidines, piperidines. Usually three-, five-, and six-membered (but not four-membered) rings being easily prepared.
References
No references
Isomerisation of alkenes

Isomerization of alkenes between cis and trans forms.
References
Solid State and Surface Photochemistry, V. Ramamurthy, Kirk S. Schanze, 2000, pg.no: 60,61,63,66;
Addition and Elimination Reactions of Aliphatic Compounds, C. H. Bamford, Charles Frank Howlett Tipper, 1973, pg.no: 300,442;
Liquid crystals: applications and uses, Birendra Bahadur, 1991, pg.no: 365.
J. Org. Chem. 2006, 71, 1055-1059.
Chem. Rev. 2003, 103, 2475-2532.
Isonitril formation

This reaction is an isonitril formation under basic condition using dichlorocarbene as reagent; dichlorocarbene is generated in situ by the phase-transfer method.
References
No references
Isothiocyanate formation from primary aromatic or aliphatic amines

Addition of primary or secondary amines to carbon disulfide yields isothiocyanates. Usually the reaction of aromatic amines with carbon disulfide goes via thiocarbamide, meanwhile the reaction with aliphatic amines goes via dithiocarbamate.
References
No references
Kolbe-Schmitt synthesis

A base-promoted carboxylation of phenols that allows the synthesis of salicylic acid derivatives. This process is known as the Kolbe-Schmitt synthesis. Carboxylation occurs at ortho position.
References
A textbook of organic chemistry, August Bernthsen, Raj K. Bansal, 2003, pg. no.421;
Organic Chemistry (Sie), Carey, pg. no. 1004;
Experiments in Green and Sustainable Chemistry, H. W. Roesky, Dietmar K. Kennepohl, Jean-Marie Lehn, 2009, pg. no. 276-277;
Name reactions: a collection of detailed reaction mechanisms, Jie Jack Li, 2006, pg. no.339;
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Chemical Reviews, 1957, 57, 583-620.
Meerwein-Ponndorf-Verley reduction

Reduction of carbonyl groups to alcohols by means of triisopropoxy aluminium.
References
No references
Menshutkin reaction

The so-called Menshutkin reaction is the conversion of tertiary amines to quaternary salts. It is an SN2 substitution between tertiary amines and alkyl halides.
References
No references
Methylation of phenols with diazomethane

Methylation of phenol with diazomethane results in the formation of methylated phenol
References
Concise encyclopedia chemistry, Mary Eagleson, 1994, pg. no.315;
Chemistry of natural products, Sujata V. Bhat, Bhimsen A. Nagasampagi, Meenakshi Sivakumar, 2005, pg. no.62;
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Chemical modification of lignocellulosic materials, David N.-S. Hon, 1996, pg. no.77.
J. Org. Chem., 1968, 33, 223–226.
Milas olefin hydroxylation

cis-hydroxylation of a double bond to a 1,2-diol with hydrogen peroxide and osmium tetroxide as catalyst.
References
Milas, W.A., J. Am. Chem. Soc., 1963, 58, 1302;
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N. A. Milas anel L. S. Maloney, ibid. 62, 184l, (1940);
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J . Org. Chem. 1990, 55, 768-770.
Milas olefin hydroxylation

cis-hydroxylation of a double bond to a 1,2-diol with hydrogen peroxide and osmium tetroxide as catalyst.
References
Milas, W.A., J. Am. Chem. Soc., 1963, 58, 1302;
Milas, W.A., J. Am. chem. Soc., 1959, 81, 3114;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302 (1936); 59, 543, 2342, 2345 (1937);
N. A. Milas, S. Sussman and H. S. Mason, J. Am. Chem. Soc. 61, 1844 (1939);
N. A. Milas anel L. S. Maloney, ibid. 62, 184l (1940);
J. W. Cook and R. Schoental, J. Chem. Soc. 1950, 47;
W. A. Waters in H. Gilman, Organic Chemistry vol. 4 (John Wiley, New York, 1953), p.1154;
J. F. Eastham, G. B. Milas and C. A. Krauth, J. Am. Chem. Soc. 81, 3114 (1959);
F. D. Gunstone in R. A. Raphael, E. C Talylor, H. Wynberg, Advances in Organic Chemistry vol.1 (Interscience, New York, 1960), p.115;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302 (1936); 59, 543, 2342, 2345 (1937);
N. A. Milas, S. Sussman and H. S. Mason, J. Am. Chem. Soc. 61, 1844 (1939);
N. A. Milas anel L. S. Maloney, ibid. 62, 184l, (1940);
J. W. Cook and R. Schoental, J. Chem. Soc. 1950, 47;
W. A. Waters in H. Gilman, Organic Chemistry vol. 4 (John Wiley, New York, 1953), p 1154;
J. F. Eastham, G. B. Milas and C. A. Krauth, J. Am. Chem. Soc. 81, 3114 (1959);
F. D. Gunstone in R. A. Raphael, E. C Talylor, H. Wynberg, Advances in Organic Chemistry vol.1 (Interscience, New York, 1960), p 115;
N. A. Milas et al., J. Am. Chem. Soc. 58, 1302; (1936); 59, 543, 2342, 2345 (1937); 61, 1844 (1939); 62, 1841 (1940);
F. D. Gunstone, Advan. Org. Chem. 1, 115 (1960); P. N. Rylander, Organic Syntheses with Noble Metal Catalysts (Academic Press, New York, 1973) p 60;
NA Milas and Sidney Sussman. J. Am. Chem. Am Chem. Soc. 1936 , 58 , 1302-1303. Soc. 1936, 58, 1302-1303;
Criegee, Ann. 1936, 522, 75;
Organic syntheses based on name reactions, Alfred Hassner, C. Stumer, pg.no: 245.
N-acylation of azides

This reaction is a direct formation of amide/peptide bonds from carboxylic acids, organic azides and Me3P. This reaction is also called catalytic Staudinger-Vilarrasa reaction.
References
Journal of Organic Chemistry, 2009, 74, 2203-2206.
Nitration of alcohols with nitric acid

Nitration of aliphatic alcohols with nitric acid in presence of sulfuric acid produces alkyl nitrates.
References
Explosive effects and applications, Jonas A. Zukas, William Walters, William P. Walters, 2002, pg. no.141;
A text book of organic chemistry, August Bernthsen, Raj K. Bansal, 2003, pg. no.394;
Canadian journal of chemistry. vol. 34. 1956, 879-884.
Nitration of alkanes

Nitration of alkane to produce nitroalkane selectively.
References
G.A. Olah, H. C. Lin, J. Am. Chem. Soc., 1971, 93, 1259;
R. Atkinson, S. M. Aschmann, W. P. L. Carter, A. M. Winer, J. N. Pitts, J. Phys. Chem., 1982, 86, 4563;
S. Sakaguchi, Y. Nishiwaki,T. Kitamura, Y. Ishii, Angew. Chem. Int. Ed., 2001, 40, 222;
S. Isozaki, Y. Nishiwaki, S. Sakaguchi, Y. Ishii, Chem. Commun., 2001, 1352;
J. Arey, S. M. Aschmann, E. S. C. Kwok, R. Atkinson, J. Phys. Chem. A., 2001, 105, 1020;
Y. Nishiwaki, S. Sakaguchi, Y. Ishii, J. Org. Chem., 2002, 67, 5663;
Modern Oxidation Methods by Jan-Erling Bäckvall, 2004, page.no: 142.
Chem. Commun., 2001, 1352–1353
Nitration of aromatic amines

Nitration of aromatic amines is an aromatic electrophile substitution. Under strong acidic conditions meta orientation is generally observed in the case of arylamines. Under less acidic conditions the free amine activates the ortho/para positions. Primary aromatic amines are usually protected with acetyl chloride or acetic anhydride, the acetamido group is ortho or para directing. Since the nitro group is deactivating, it is usually easy to stop the reaction after one group has entered the ring. The attecking species is nitronium ion (NO2+), which can be formed with HNO3 + H2SO4 or cc. HNO3or N2O5 in CCl4 or with micellaneous etc.
References
No references
Nitration of aromatic hydrocarbons

Aromatic organic compounds are nitrated via an electrophilic aromatic substitution mechanism involving the attack on electron-rich benzene ring by the nitronium ion.
References
Comprehensive Practical Organic Chemistry: Preparation and Quantitative Analysis, V. K. Ahluwalia, R. Aggarwal, 2001, pg. no: 152;
Organic chemistry, Marye Anne Fox, James K. Whitesell, 2004, Pg. no: 556;
Advanced Organic Chemistry: Structure and mechanisms, Francis A. Carey, Richard J. Sundberg, 2007, Pg. no: 793;
The nitro group in organic synthesis, Noboru Ono, 2001, Pg. no: 4.
Tetrahedron Letters 48 (2007) 8659–8664.
Tetrahedron Letters 47 (2006) 4933–4935.
Nitrosation of secondary amines

Nitrosation of secondary amines leading to N-nitrosoamines, which are carcinogenic and mutagenic agents. The nitrosation reactant is nirtosyl cation which is formed in situ. The reaction is usually accomplished by using nitrosating agents such as nitrous acid, NaNO2/HCl, nitrogen oxides (NO, N2O3 or N2O4), peroxynitrite, alkyl nitrites, nitrosyl chloride (NOCI), nitosonium tetrafluoroborate (NOBF4), [NO+-crown-H(NO3)2 -], Fremy’s salt, oxyhyponitrite (N2O3),or Angeli’s salt (Na2N2O3). Primary amines form diazonium salts. Tertiary aliphatic amines undergo cleavage to form N-nitrosoamines and oxocompounds, tertiary aryl amines undergo nitrosation of the ring.
References
No references
Nucleophile acylation with carboxylic acid or anhydride

Acylation of alcohol with acyl anhydride or carboxylic acid.
References
Journal of Molecular Catalysis A: Chemical 181 (2002) 207–213;
Chemistry and chemical reactivity, Volume 2, John C. Kotz, Paul Treichel, John R. Townsend, 2008, pg. no.472;
Invitation to organic chemistry, A. William Johnson, 1999, pg. no.556;
E. J. Chem., 5, 2008, 641-647;
General organic and biological chemistry, Kenneth W. Raymond, 2009, pg. no.266;
Comprehensive Practical Organic Chemistry: Preparation and Quantitative Analysis, V. K. Ahluwalia, R. Aggarwal, 2001, pg. no.101;
J. Am. Chem. Soc., 103, 5972, (1981).
Nucleophilic aromatic substitution (SN2)

Aryl halides undergo nucleophilic aromatic substitution under certain conditions, where the reactive agent is an electron donor, while the leaving group is a halogen ion. The larger the number of electron withdrawing substituents on the ring, especially in the positions ortho and para to the point of substitution, the greater the rate of reaction.
References
Organic chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no.858;
Organic chemistry demystified, D. R. Bloch, 2006;
Advanced organic chemistry: reactions and synthesis, Francis A. Carey, Richard J. Sundberg, pg. no.724;
Microscale organic laboratory: with multistep and multiscale syntheses, Dana W. Mayo, Ronald M. Pike, David C. Forbes, 2010, pg. no.385;
Principles of organic synthesis, Richard Oswald Chandler Norman, James M. Coxon, 1993, pg. no.400, 401;
Advanced organic chemistry: reactions and mechanisms, Singh, 2007, pg. no.332;
Comprehensive organic synthesis: additions and substitutions at c-c pi bonds, M. Trost, Ian Fleming, Martin F. Semmelhack, 1991, pg. no.433;
Organic Chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no.859.
Oppenauer oxidation

A mild oxidation of alcohols to aldehydes or ketones, using metal (Al, K) alkoxydes and a aldehyde or ketone.
References
No references
Oxidation of alcohols

Alcohols can be oxidized to aldehydes or carboxylic acids or to ketons.
References
Reactions and syntheses in the organic chemistry laboratory By Lutz-Friedjan Tietze, Theophil Eicher, Ulf Diederichsen, Andreas Speicher, 2007, pg. no.216;
Advanced Organic Chemistry Part B: Reactions and synthesis By Francis A. Carey, Richard J. Sundberg, 2007, pg. no.1068;
Reagents for organic synthesis, Volume 1, Louis Frederick Fieser, 1969, pg. no.142;
Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Jie Jack Li, 2009, pg. no.305
Oxidation of alcohols to aldehydes and ketones: a guide to current common practice, Gabriel Tojo, Marcos Fernandez, 2006, pg. no.15, 23, 24;
Organic Synthesis: concepts and methods, Jorgen-Hinrich Fuhrhop, Guangtao Li, pg. no.189.
Oxidation of aldehydes

The reaction is done under acidic conditions and the aldehyde is oxidized to a carboxylic acid. (Under alkaline conditions a salt is formed instead).
References
No references
Oxidation of alkanes to alcohols

Oxidation reaction of alkanes to produce alcohols selectively.
References
K. Wiberg, G. Foster, J. Am. Chem. Soc., 1961, 83, 423;
S. Yiu, Z. Wu, C. Mak, T. Lau, J. Am. Chem. Soc., 2004, 126, 14921;
B.C. Bales, P. Brown, A. Dehestani, J.M. Mayer, J. Am. Chem. Soc., 2005, 127, 2832;
T. M. Hellmann, G.A. Hamilton, J. Am. Chem. Soc., 1974, 96, 5, 1530;
K. Tanemura, T. Suzuki, Y. Nishida, K. Satsumabayashi, T. Horaguchi, J. Chem. Soc. Perkin Trans. I., 2001, 3230;
US 5017731, 1991;
Ruthenium in Organic Synthesis, Shun-Ichi Murahashi(Ed.) , 2004, pg.no: 69, 83;
Green Chemistry and Catalysis, Roger Arthur Sheldon, Isabel Arends, Ulf Hanefeld, 2007, pg.no: 163.
Oxidation of alkanes to ketones

Oxidation reaction of alkanes to produce ketones selectively.
References
C.C. Hobbs, B. Houston, J. Am. Chem. Soc., 1954, 76, 1254;
W.F. Sager, A. Bradley, J. Am. Chem. Soc., 1956, 78, 1187;
Y. Ishii, T. Iwahama, S. Sakaguchi, K. Nakayama, Y. Nishiyama, J. Org. Chem., 1996, 61, 4520;
S. Yiu, Z. Wu, C. Mak, T. Lau, J. Am. Chem. Soc., 2004, 126, 14921.
Oxidation of alkenes with peracids

Oxidation of alkenes with peracid yields epoxides.
References
Oxidation and Reduction in Organic Synthesis, Timothy J.Donohoe, pg.no: 14;
Modern Methods of Organic Synthesis, William Carruthers and Iain Coldham, 2004, pg.no: 332, 333;
Synthetic Approaches in Organic Chemistry, Raj K. Bansal, pg.no: 72;
Asymmetric Organocatalysis, Albrecht Berkessel, Harald Gröger, David MacMillan, pg.no: 292.
J. Org. Chem. 1999, 64, 196-201.
Oxidation of alkenes with potassium permanganate

Acidified potassium permanganate solution oxidises alkenes to carboxylic acids.
References
Organic Chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 213;
Organic Chemistry, Marye Anne Fox, James K. Whitesell, 2004, pg.no: 501.
J. Org. Chem., 1977, 42, 3749-3753.
Oxidation of alkynes with potassium permanganate(basic medium)

Alkynes on treatment with alkaline potassium permanganate undergo oxidative cleavage at triple bond to form carboxylic acids. The position of the triple bond determines the resulting carboxylic acids.
References
Organic Reaction Mechanisms, V. K. Ahluwalia, R. K. Parashar, 2003, pg.no: 142;
Organic Chemistry, Bhupinder Mehta, Mehta & Mehta, 2004, pg.no: 261.
Vogel's Textbook of Practical Organic Chemistry, fifth edition, p. 670.
J Org Chem, 1979, 44, 2726-2730.
J Org Chem, 1985, 50, 4306-4309.
Oxidation of alkynes with potassium permanganate(neutral medium)

Internal alkynes on oxidation with potassium permanganate under mild conditions forms diketones.
References
Organic Reaction Mechanisms, V. K. Ahluwalia, R. K. Parashar, 2003, pg.no: 142;
Advanced organic chemistry, Francis A. Carey, Richard J. Sundberg, 2007, pg.no: 1075;
Hydrocarbon chemistry, Árpád Molnár, 2003, pg.no: 489.
J Org Chem, 1979, 44, 1574.
Oxidation of alpha methyl aromatic hydrocarbons with KMnO4 to benzoic acid

Alkyl benzenes undergo oxidation with strong oxidizing agent, KMnO4. The benzene ring is unchanged but the alkyl group is oxidized. All carbons of the alkyl group except that attached to the ring are oxidized to CO2. The carbon attached to the ring is oxidized to the highest oxidation state possible (COOH group) with out breakage of the bond to the aromatic ring.
References
Comprehensive Practical Organic Chemistry, V.K. Ahluwalia, R. Aggarwal, 1905, Pg. no: 159-160;
Organic Chemistry, Manju Mehta, 2005, Pg. no: 291;
A textbook of organic chemistry, August Bernthsen, Raj K. Bansal, Ed. 4, 2003, Pg. no: 314;
The organic chemistry problem solver, Max Fogiel, 2001, Pg. no: 402-403;
Schaum's outline of theory and problems of general, organic, and biological, George G. Odian, Ira Blei, 1994, Pg. no: 237.
Organic Synthesis, 1955, 3, p791.
Oxidation of anilines to ortho quinones

Ortho and para aromatic diamines are easily oxidized to ortho- and para-quinones. Either or both NH2 groups can be replaced by OH groups to give the same products, but for the preparation of ortho-quinones only OH groups are normally satisfactory. The reaction has been successfully carried out with other groups para to OH or NH2: halogen, OR, Me, f-Bu, and even H. Many oxidizing agents have been used: acid dichromate, silver oxide, silver carbonate, lead tetraacetate, HIO4, dimethyl dioxirane, and atmospheric oxygen etc. A particularly effective reagent for rings with only one OH or NH2 group is (KSO3JN—O- (dipotassium nitrosodisulfonate; Fremy's salt), which is a stable free radical. Phenols, even some whose para positions are unoccupied, can be oxidized to ortho-quinones with diphenylseleninic anhydride.
References
No references
Oxidation of anilines to para quinones

Ortho and para aromatic diamines are easily oxidized to ortho- and para-quinones. Either or both NH2 groups can be replaced by OH groups to give the same products, but for the preparation of ortho-quinones only OH groups are normally satisfactory. The reaction has been successfully carried out with other groups para to OH or NH2; halogen, OR, Me, f-Bu, and even H. Many oxidizing agents have been used: acid dichromate, silver oxide, silver carbonate, lead tetraacetate, HIO4, dimethyl dioxirane, and atmospheric oxygen etc. A particularly effective reagent for rings with only one OH or NH2 group is (KSO3JN—O- (dipotassium nitrosodisulfonate; Fremy's salt), which is a stable free radical. Phenols, even some whose para positions are unoccupied, can be oxidized to ortho-quinones with diphenylseleninic anhydride.
References
No references
Oxidation of phenols to ortho or para quinones

Oxidation of phenols with K2Cr2O7/ H2SO4 or AgO yields conjugated dicarbonyl compounds called quinones.
References
Organic chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no. 813;
General organic and biological chemistry, Kenneth W. Raymond, 2009, pg. no.271;
General guidelines for synthesis and purification of Quinone compounds, pg. no.1, 2.
Organic Synthesis, 1941, 1, p. 482.
Oxidation of tertiary amine to amine oxide

Oxidation reaction of tertiary amines to amine oxides using oxidating agent.
References
No references
Oxidation of vicinal diols to aldehydes or ketones

1, 2- diols (vicinal diols) undergo oxidation to form aldehydes or ketones.
References
Org. Lett., 1999, 1 (5), pp 713–715;
Handbook of Reagents for Organic Synthesis: Reagents for high-throughput solid-phase and solution-phase organic synthesis by Peter Wipf, 1999, pg. no.309;
Principles of organic synthesis, Richard Oswald Chandler Norman, James M. Coxon, 1993, pg. no.616;
Organic chemistry, Dhawan, 2007, pg. no.7-25;
Organic chemistry demystified, D. R. Bloch, 2006, pg. no.310;
Organic chemistry, Thomas N. Sorrell, 2006, pg. no.343.
Ozonolysis of alkenes

Ozone is an electrophilic reagent that reacts with carbon-carbon double bonds by a 1,3-dipolar cycloaddition reaction followed by rearrangement reaction to form ozonides. The resulting ozonides can be cleaved oxidatively or reductively to carboxylic acids, ketones, aldehydes or alcohols. The nature of the products formed depends on the structure of the alkene.
References
Oxidation and Reduction in Organic Synthesis, Timothy J.Donohoe, 2003, pg.no: 37;
Organic chemistry, Marye Anne Fox, James K. Whitesell, pg.no: 503;
Modern Methods of Organic Synthesis, William Carruthers and Iain Coldham, 2004, pg.no: 360.
Organic Letters 2006, 8, 3199-3201.
Paal-Knorr pyrrole synthesis

Paal-Knorr pyrrole synthesis is the condensation of a 1,4-dicarbonyl compound with an excess of a primary amine or ammonia to give a pyrrole.
References
Tetrahedron, 2006, 47, 5383-5387.
Paal-Knorr thiophene synthesis

Paal-Knorr synthesis allows to generate 5 membered heterocyclic rings such as thiophenes, furans or pyrrols from 1,4-diketones. Thiophene synthesis is a condensation reaction of 1,4-dicarbonyl compound in the presence of an excess of a source of sulfur such as phosphorous pentasulfide or Lawesson's reagent - the latter acts as sulfurizing agents as well as dehydrating agents.
References
Journal of Organic Chemistry, 2008, 73, 3377-3383.
Petasis reaction

The Petasis Reaction (or the so-called boronic acid Mannich reaction) is a multicomponent reaction for coupling of an amine, aldehyde, and vinyl- or aryl-boronic acid to form substituted amines. The direct reaction with glyoxylic acid leads to unnatural α-amino acids in a single step, while avoiding the appearance of toxic side products.
References
No references
Phenol formation from primary anilines

Conversion of aniline to phenol can be achieved by treating aniline with NaNO2+ acid (diazotisation) than treat it with base like NaOH/KOH or simple H2O.
References
No references
Pictet Spengler isoquinoline synthesis

The Pictet-Spengler reaction is one of the key methods for construction of the isoquinoline skeleton. This reaction involves the condensation of a beta-arylethylamine with an aldehyde, ketone, or 1,2-dicarbonyl compound to give the corresponding tetrahydroisoquinoline. These reactions are generally catalyzed by protic or Lewis acids, although numerous thermally-mediated examples are found in the literature. Aromatic compounds containing electron-donating substituents are the most reactive substrates for this reaction.
References
Chinese Chemical Letters, 2004, 15, 505-507.
Reaction of alkynes with oxo compounds (Reppe like reaction)

Oxo compounds participate in acetylide addition to afford the corresponding propargyl alcohols.
References
Industrial organic chemicals, Harold A. Wittcoff, Bryan G. Reuben, Jeffrey S. Plotkin, 2004, pg.no: 352;
Acetylene chemistry, François Diederich, Peter J. Stang, Rik R. Tykwinski, 2005, pg.no: 104, 116, 117, 118, 119, 121, 123, 124.
Reaction of amines with alcohols

The alkylation of amines by alcohols with loss of water is a thermodynamically favored process where the loss of a carbon-oxygen bond for forming a carbon-nitrogen bond is compensated by the gain of an oxygen-hydrogen bond from a nitrogen-hydrogen bond. The reaction can be performed using heterogeneous or homogeneous catalysis.
References
No references
Reaction of primary aliphatic amines with nitrous acid

Low molecular weight primary aliphatic amines would react easily with nitrous acid to form primary alcohols. The oxidative deamination of aliphatic amines by nitrous acid results in alcohol, and nitrogen gas and water as side products.
References
No references
Reduction of alkyl halides (Zn/H+,LiAlH4,Pd/C,HI)

Alkyl halides undergo reduction by suitable reducing agents such as LiAlH4, Zn/H+, Pd/C & HI/red phosphorus to form corresponding alkanes.
References
Comprehensive organic synthesis: Selectivity, Strategy, and Efficiency in Modern Organic Chemistry, Barry M. Trost, Ian Fleming,1991, pg. no: 795, 803;
Organic chemistry, 8th edition, Solmons G, 2009, pg. no:51;
The essentials of organic chemistry, Max Fogiel, Research and education association, 1995, pg. no:14;
Comprehensive organic functional group transformations, Alan R. Katritzky, Otto Meth-Cohn, Charles Wayne Rees, 1995, pg. no:3;
A text book of organic chemistry, August Bernthsen, Raj K Bansal, pg. no:161;
Organic chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no:145;
Chemistry, Arun Mittal, 2007, pg. no:394;
Organic chemistry I, Max Fogiel, research and education association, 1994, pg. no:32.
Mandai, McMurray, J Org Chem, 2007, 72, 6556-6561.
J. Org. Chem. 1982,47, 276-280.
Reduction of carboxylic acids to primary alcohols

Carboxylic acids are reduced to primary alcohols by several catalysts, the most common and powerful reducing agent is lithium aluminum hydride. Aldehyde is formed first and then a primary alcohol. Because LiAlH4 reacts rapidly with aldehydes, it is impossible to stop at the halfway stage. LiAlH4 reacts violently with water and so the reactions are carried out in solution in dry solvent (Et2O or THF). The reaction happens at room temperature; the product is a complex aluminium salt that is converted into the alcohol by acidic workup.
References
Indian Pat. Appl., 2007CH01104, 06 Feb 2009, Chakrabarti, Dhurjati Prasad et al
Reduction of nitriles

Aliphatic or aromatic nitriles can be reduced to primary amine with a suitable chemical reagent. Typical reagent is LiAlH4 in ether solvent followed by aqueous work-up. Catalytic hydrogenation (H2 / catalyst) can also be used giving the same products. Nitriles can also be reduced to aldehydes. One method is called the Stephen aldehyde synthesis.
References
Green Chemistry, 2010, 12(1), 87-93.
Reduction of nitro arenes to azo arenes

Reduction of aromatic nitro compound with different reducing agents yields aryl azo compound.
References
Treatise on general and industrial organic chemistry, Molinari Ettore, 2009, pg. no.565;
Tellurium in organic synthesis, Nicola Petragnani, Hélio A. Stefani, 2007, pg. no.122;
Comprehensive organic synthesis: selectivity, strategy, and efficiency in Modern Organic Chemistry, Barry M. Trost, Ian Fleming, 1991, pg. no.364;
Bull. Chem. Soc. Jpn., 69, No.2 (1996);
Electrolytic preparations: Exercises for use in the laboratory by chemists, Robert Salmon Hutton Karl Elbs, 2009, pg. no.79.
Organic Synthesis, 1955, 22, p28.
Reduction of nitro compounds to amines or anilines

The reduction of nitro compounds in presence of metal catalyst (Fe/HCl, H2/Raney Ni, Sn/HCl, SnCl2/HCl etc.) to give primary amines.
References
Organic chemistry II, Max Fogiel, 2000, pg. no.79;
The nitro group in organic synthesis By Noboru Ono,2001, pg. no. 172, 174;
Organic chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no.788;
Organic chemistry, Dhawan, 2007, pg. no.9-71.
Teaching of Chemistry Pr By P.b.samnani, 2009, pg. no.102;
Use of polymer-supported amines in the catalytic nitr-aldol reaction of nitroalkanes with aldehydes, Francisco Palacios, Jesus M. de los Santos, and Domitila Aparicio, 28 th June 2005, pg. no.5;
E-Journal of chemistry, vol 5, pp. 914-917, October 2008.
J. Org. Chem. 2009, 74, 6960–6964.
Ring closure by halogen elimination from alkyl halides

Dihaloalkanes (two halogens are present at two terminals) on reaction with Na or Zn metal undergo intramolecular cyclization to produce cycloalkanes.
References
Hydrocarbons (Alkanes, Alkenes And Alkynes), Amit Arora, 2006, pg. no. 2;
The essentials of organic chemistry, Max Fogiel, Research and Education Association, pg. no. 48;
Organic Chemistry for advanced students, Julius Berend Cohen, 2009, pg. no. 189;
Organic Chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no. 173
Organic Syntheses, 1973, 5, 328; 1964, 44, 30.
Ritter reaction of alkenes

Synthesis of amides from nitriles and alkenes under strongly acidic media.
References
J.J. Ritter, P.P. Minieri, J. Am. Chem. Soc., 1948, 70, 4045;
J.J. Ritter, J. Kalish, J. Am. Chem. Soc., 1948, 70, 4048;
L.S. Hegedus, T.A. Mulhern, H. Asada, J. Am. Chem. Soc., 1986, 108, 20, 6224-6228;
C.L. McCormick, C.B. Johnson, J. Macromol. Sci.-Chem.A. 1990, 27, 5, 539;
W.M. Samaniego, Tetrahedron Lett., 1994, 35, 6967;
M. Camail, A. Margaillan, S.Turet, J.L. Vernet, Eur. Polymer J., 1998, 34, 11;
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L. Castellanos, C. Duque, J. Rodríguez, C. Jiménez, Tetrahedron, 2007, 63, 7, 1544-1552;
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Name Reactions, Jie Jack Li, pg.no: 501.
J. Org. Chem. 2009, 74, 2207–2209.
Eur. J. Org. Chem. 2007, 4642–4645.
SN1 substitution of alkyl halides

In the SN1 reaction, a planar carbenium ion is formed first, which then reacts further with the nucleophile. Since the nucleophile is free to attack from either side, this reaction is associated with racemization. SN1 reactions work best with weak nucleophiles. Typical polar protic solvents include water and alcohols, which will also act as nucleophiles.
References
Chemistry for pharmacy students: general, organic and natural product chemistry, Satyajit D. Sarker, Lutfun Nahar, 2007, pg. no. 233;
Organic Chemistry, Joseph M. Hornback, 2005, Ed. 2, pg. no. 278;
Advanced Organic Chemistry: Reactions and Mechanisms, Singh, pg. no. 97;
Organic Chemistry, 8th Edition, Solomons & Fryhle, pg. no. 257;
Organic Chemistry (Sie), Carey, pg. no. 334;
Organic Chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no. 343.
Orgnic Letters, 2002, 4, 343-345.
SN2 substitution of alkyl halides

SN2 is a bimolecular, nucleophilic substitution reaction. In a bimolecular mechanism, the attack of nucleophile on sp3 hybridized carbon of alkyl halide and removal of halide ion (leaving group) occurs simultaneously in a single step. Thus, nucleophile has no other option but to attack the carbon from a side opposite to halogen (leaving group). SN2 mechanism involves the inversion of configuration (also known as Walden Inversion).
References
Advanced organic chemistry: reactions and mechanisms, Singh, 2007, pg. no. 94, 98, 104;
Organic chemistry, 8th edition, Solomons & Frryhle, 2009, pg. no. 245, 250, 251;
Organic chemistry, Marye Anne Fox, James K.Whitesell, 2004, pg. no. 42;
Modern physical organic chemistry, Eric V. Anslyn, Dennis A. Dougherty, pg. no. 638;
Organic chemistry (Sie), Carey, 2008, pg. no. 338;
Organic chemistry, J. William Suggs, 2001, pg. no.123.
Schotten-Baumann reaction

The nucleophilic acyl substitution reaction of carboxylic acids and amines is a method for amide synthesis; in practice amides are more readily prepared from the more reactive acyl chlorides.
References
Synthetic Communication, 2009, 39, 2694-2701.
Schotten-Baumann reaction with phenols

Phenol reacts with acid chlorides (or acid anhydrides) in alkali solution to form phenylesters (acylation). This reaction is called Schotten-Baumann reaction.
References
Practical pharmaceutical chemistry - II, Dr. A. V. Kasture, Dr. S. G. Wadodkar, 2008, pg. no.53;
Comprehensive practical organic chemistry: Preparation and quantitative analysis, V. K. Ahluwalia, R. Aggarwal, 2001, pg. no.101;
Organic Chemistry (Sie), Carey, 2008, pg. no.1001;
Comprehensive Practical Organic Chemistry: Qualitative Analysis, V.K. Ahluwalia, S. Dhingra, 2004, pg. no. 57;
Practical organic chemistry, Frederick George Mann, Bemard Charles Saunders, 1960, pg. no 110.
Sulfation of alcohols with sulfuric acid

Sulfation of alcohols with sulfuric acid to produce alkyl hydrogen sulfates.
References
Aliphatic organic chemistry, Amit Arora, 2006, pg. no.84;
Organic Chemistry, Bhupinder Mehta, Manju Mehta, 2005, pg. no.437;
Chemistry, Kenneth W. Whitten, Raymond E. Davis, M. Larry Peck, George G. Stanley, 2009, pg. no.1017;
Polysaccharides: structural diversity and functional versatility, Severian Dumitriu, 2005, pg. no.1181;
Characterization of organic compounds by chemical methods: an introductory laboratory text book, Terence C. Owen, 1969, pg. no.55.
BAYER CROPSCIENCE AG Patent: WO2007/22900 A1, 2007;
Sulfonation of aromatic amines

Arylamines are very reactive toward electrophilic aromatic substitution. It is customary to protect arylamines as their N-acyl derivatives before carrying out ring nitration, chlorination, bromination, sulfonation, or Friedel–Crafts reactions.
References
No references
Sulfonation of aromatic hydrocarbons

Reaction of aromatic hydrocarbons with sulfuric acid produces corresponding sulfonic acids. It is an electrophilic substitution reaction in which a hydrogen atom on an arene is replaced by a sulfonic acid functional group.
References
Synthetic approaches in organic chemistry, Raj K. Bansal, 1996, pg. no: 370;
Riegel's handbook of industrial chemistry, Emil Raymond Riegel, James Albert Kent, 2003 pg. no: 922;
Chlorosulfonic acid: a versatile reagent, Richard James William Cremlyn, Royal Society of Chemistry (Great Britain), 2002, pg. no: 45, 46:
J Am Chem Soc, 1982, 47, 4075-4081.
Symmetric coupling of 1-alkynes

Terminal alkynes or 1-trimethylsilyl alkynes can be coupled by heating with stoichiometric amounts of cupric salts in pyridine or similar base to produce symmetrical diynes in high yields.
References
Comprehensive organic functional group transformations, Alan R. Katritzky, Otto Meth-Cohn, Charles Wayne Rees, 1995, pg. no: 1035;
Name Reactions, Jie Jack Li, 2006, pg.no: 265;
Name Reactions and Reagents in Organic Synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, Frank G. Favaloro, Jr, 2005, pg.no: 225;
Acetylene Chemistry, François Diederich, Peter Stang, Rik R. Tykwinski, 2006, pg.no: 374;
M.H.Haley, M.L.Bell, S.C.Brand, D.B.Kimball, J.J.Pak, W.B.Wan,Tetrahedron Letters 1997,38,7483;
F.Jung, A.Berger,J.-F.Biellmann, Organic Letters 2003, 5,383.
Symmetric coupling of di-alkynes

Oxidative coupling of terminal di-alkynes with a stoichiometric amount of a copper(II) salt in pyridine.
References
Modern supramolecular chemistry: strategies for macrocycle synthesis, François Diederich, Peter J. Stang, Rik R. Tykwinski, 2008, pg.no: 190;
Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, 2005, pg.no: 224, 225;
S.Hoger, K.Bonard, L.Karcher, A.D.Meckenstock, Journal of Organic Chemistry 2000, 65, 1588;
F.Toda, Y.Tokumaru, Chemistry Letters 1990, 987;
Acetylene Chemistry, François Diederich, Peter Stang, Rik R. Tykwinski, 2006, pg.no: 346, 374, 375;
Some modern methods of organic synthesis, W. Carruthers, 1971, pg.no: 50.
J. Org. Chem. 2006, 71, 4544-4548.
Synthesis of acid anhydrides

Acid anhydrides are one of the most reactive carboxylic acid derivatives and are synthesized by nucleopilic substitution reaction.
References
No references
Synthesis of acid bromides

Synthesis of acyl bromides from carboxylic acids is a nucleophylic acyl substitution reaction. PBr3, as a strong reducing and the most common brominating agent converts carboxylic acids to carboxylic acid bromides. An acyl bromide can readily exist in the enol form, and this tautomer is rapidly brominated at the α-carbon. Other possible brominating agents: PBr5, Br2, NBS etc. Acyl bromides are rarely made in comparison with acyl chlorides.
References
No references
Synthesis of acid chlorides

Synthesis of acyl chlorides from carboxylic acids by treating them with thionyl chloride (SOCl2), or phosphorus trichloride (PCl3), or phosphorus pentachloride (PCl5) is a nucleophylic acyl substitution reaction. The reaction is usually catalyzed by dimethylformamide.
References
No references
Synthesis of cyclic anhydrides

Cyclic anhydrides containing five- and six-membered anhydride rings are readily prepared from their corresponding dicarboxylic acids. This reaction is so facile, that in some cases it occurs on heating the dicarboxylic acid. POCl3, P2O5 or acetic anhydride can also be used for the formation of cyclic anhydrides. Anhydrides are typically not target molecules, but rather they are used as intermediates for the synthesis of other organic members such as esters and amides for the industrial applications include dyes, pharmaceuticals, pesticides, plastics, fibers, curing agents, plasticizers and many others. Phthalic anhydride is a versatile intermediate in organic chemistry, in part because it is bifunctional and cheaply available.
References
No references
Tetrazole synthesis

Azide ions (e.g. sodium azide in DMF) react with nitriles in a [3+2] cycloaddition with formation of 5-substituted 1-H tetrazoles. Cycloaddition of alkyl-, aryl- or trimethylsilyl azide with nitriles or isonitriles yields 1,5- and/or 2,5-disubstituted tetrazoles.
References
European Journal of Organic Chemistry, 2003, (5), 885-893.
Tosylation with Koser's reagent

Vic-bis tosylation of alkenes by means of hydroxytosyloxyiodobenzene.
References
Koser, G.F., J. Org. Chem., 1977, 42, 1476;
Neiland, O., J. Org. Chem. USSR(Eng.), 1970, 6, 889;
Koser, G.F., J. Org. Chem., 1980, 45, 1542;
Koser, G.F., J. Org. Chem., 1984, 49, 2462;
Papoutsis I. Spyroudis S. Varvoglis A, Tetrahedron, 1998, 54, 1005-1012;
Wirth Yusubov, Org. Lett., 2005, 7, 519;
Organic syntheses based on name reactions, Alfred Hassner, C. Stumer, 2002, pg.no: 206;
Cyclopropanation of alkenes using hypervalent iodine reagents, Andreas S. Biland,a Sabine Altermann,b and Thomas Wirtha,b;
Hirt, U. H.; Spingler, B.; Wirth, T. J. Org. Chem. 1998, 63, 7674.
Transesterification reaction

The reaction is an interchange of an organic ester groups into another ester of the same acid with an alcohol in the presence of a acid, base or enzyme catalysis. The acid catalyzed mechanism for this transesterification simply consists of adding one alcohol and eliminating the other.
References
Synthetic Communications, 2010, 40(11), 1670-1676.
Ullmann reaction

The Ullmann reaction is the synthesis of biaryls from aryl halides via copper-catalyzed coupling. In this reaction, the first step is the oxidative addition of the copper into the aryl halide. The copper (I) aryl species then undergoes oxidative coupling with another equivalent of the aryl halide resulting in a biaryl copper compound. Reductive elimination follows resulting in the formation of the carbon- carbon bond. The reaction is limited to electron deficient aryl halides and requires harsh reaction conditions.
References
F. Ullmann, Justus Liebigs Ann. Chem., 1904, 232, 38;
F. Ullman, Bielecki, Ber., 1901, 34, 2174;
R.C. Fuson, E.A. Cleveland, Organic Syntheses, Coll. Vol. 3, p.339; Vol. 20, p.45;
F. Ullmann, P. Sponagel, Ber, 1946, 38, 407;
P.E. Fanta, Chem. Revs., 1946, 38,139;
P.E. Fanta,Synthesis, 1974, 9;
L.M. Stark, X.-F. Lin, L.A. Flippin, J. Org. Chem., 2000, 65, 3227;
K.D. Belfield, K.J. Schafer, W. Mourad, B.A. Reinhardt, J. Org. Chem., 2000, 65, 4475;
S. Venkatraman, C.-J. Li, Tetrahedron Lett, 2000, 41, 4831;
J.M. Farrar, M. Sienkowska, P. Kaszynski, Synth. Commun, 2000, 30, 4039;
D. Ma, C. Xia, Org. Lett., 2001, 3, 2583;
E. Buck, Z.J. Song, D. Tschaen, P.G. Dormer, P.J. Reider, Org. Lett., 2002, 4, 1623;
A. Hameurlaine, W. Dehaen, Tetrahedron Lett, 2003, 44, 957;
Name Reactions for Homologation, Jie Jack Li, E. J. Corey, 2009, Pg. no: 258- 259;
Synthesis of biaryls, Ivica Cepanec, 2004, Pg. no: 10, 13-15, 15-16, 32;
Name Reactions for Homologation, Jie Jack Li, E. J. Corey, 2009, Pg. no: 261.
Advances in heterocyclic chemistry, Alan R. Katritzky, 1984, Pg. no: 121;
Name reactions and reagents in organic synthesis, Bradford P. Mundy, Michael G. Ellerd, Frank G. Favaloro, 2005, Pg. no: 663;
A. I. Meyers, J. J. Willemsen, Tetrahedron Letters 1996, 37, 791.
Wacker-Tsuji olefine oxidation

Oxidation of alkenes to ketones in the presence of Pd(II) catalysts. The oxidation of ethylene to acetaldehyde employing palladium chloride and cupric chloride as catalysts and molecular oxygen as oxidant. The reaction has been extensively developed for the oxidation of terminal alkenes to methyl ketones.
References
F.C. Phillips, Amer. Chem. J., 1984, 14, 255;
J. Tsuji, et al., Tetrahedron Lett., 1982, 23, 2679;
J. Smidt, (Wacker), Angew. Chem., 1959, 71, 176;
J. Tsuji, et al. Synthesis, 1984, 369;
D.D.M. Wayner, J. Org. Chem., 1990, 55, 2924;
Application to hydroxy-alpha,beta-unsaturated esters: S. X. Auclair et al., Tetrahedron Letters 33, 7739 (1992);
Use of a multicomponent catalytic system: E. Monflier et al., ibid. 36, 387 (1995);
Synthetic applications: M. Romero et al., ibid. 35, 3255 (1994);
L.A. Paquette, X. Wang, J. Org. Chem. 59, 2052 (1994);
Reviews: L. S. Hegedus, Comp. Org. Syn. 4, 552-559 (1991);
J. Tsuji, ibid. 6, 449-468;
J. Smidt et al., Angew. Chem. Int. Ed. 1, 176 (1959);
S. X. Auclair et al., Tetrahedron Letters 33, 7739 (1992) ;
E. Monflier et al. Tetrahedron Letters, 36, 387 (1995) ;
M. Romero et al., Tetrahedron Letters, 35, 3255 (1994);
L. A. Paquette, X. Wang, J. Org. Chem. 59, 2052 (1994) ;
L. S. Hegedus, Comp. Org. Syn. 4, 552-559 (1991);
J. Tsuji, Comp. Org. Syn. 6, 449-468(1991);
J. Tsuji, M. Minato, Tetrahedron Letters, 28, 32, 1987, 3683-3686;
J. Tsuji, H. Nagashima,K Hori, Tetrahedron letters, 23, 26, 1982, 2679-2682;
G. Cum, R. Gallo, S. Ipsale, A. Spadaro, J. Chem. Soc. Chem. Commun., 22, 1985, 1571-1573;
Modern Methods of Organic synthesis, William Carruthers and lain Coldham, 2004, pg.no: 366, 367;
Name Reactions of Functional Group Transformations, Jie Jack Li, E.J.Corey, 2007, pg.no: 319;
Advanced Organic Chemistry, Francis A. Carey, Richard J. Sundberg, 2007, pg.no; 711;
Hydrocarbon chemistry, Goerge A Olah, Arpad Molnar, 2003, pg.no: 526.
Water addition to carbonyl compounds

Nucleophilic addition of water to carbonyl group of aldehydes and ketones is an equilibrium reaction which depends strongly on the structure and steric hindrance of the carbonyl compoound. Electron withdrowing groups can increase the extent of hydration. The reaction goes via either acid or base catalysis. The extent of hydration decreases as the number of alkyl groups on the carbonyl increase, thats why aldehydes react faster than ketones. Aryl aldehydes and ketones have relatively unfavorable hudration equlibria. The relative rate of addition cab be predicted from the trends in equlibrium constants. Hydrates are usually stable in water solution and decompose on distillation.
References
No references
Williamson ether synthesis

In Williamson synthesis, ethers can be prepared by reaction of alkoxide (alcoholate) or phenoxide with an alkyl halide.
References
A text book of organic chemistry for students of medicine and biology, Elmer Verner McCollum, 2008, pg. no:51;
Organic chemistry, 8th edition, Solomons & Fryhle, 2009, pg. no:512;
Organic chemistry, William H. Brown, Christopher S. Foote, Brent L. Iverson, Eric V. Anslyn, 2008, pg. no: 445;
The organic chemistry problem solver, volume 2, Max Fogiel, research and education association, 1994, pg. no. 491, 492;
Microscale organic laboratory: With multistep and multiscale syntheses, Dana W. Mayo, Ronald M. Pike, David C. Forbes, 2010, pg. no.321;
Organic chemistry (Sie), Carey, 2008, pg. no.670, 671.
Organic Syntheses, 1990, 7, p386.
Wittig reaction

The Wittig reaction uses phosphorus ylides (Wittig reagents) to convert aldehydes and ketones to alkenes. The double bond connects the carbon of the original C=O group of the aldehyde or ketone and the negatively charged carbon of the ylide. The reaction is carried out under strong basic conditions. The most attractive feature of the Wittig reaction is its regiospecificity. With simple ylides this results in almost exclusively the Z-alkene product. With semistabilized or stabilized ylides this results in E-alkene product.
References
No references
Wolff-Kishner reduction

The Wolff-Kishner reaction is a selective carbonyl hydrogenation leaving unsaturations and esters intact. The originally method involved heating an aldehyde or a ketone with hydrazine (H2NNH2) and sodium or potassium hydroxide in a high-boiling alcohol such as triethylene glycol converts the carbonyl to a CH2 group. This reaction is an extension of imine formation, because hydrazone is an intermediate in the reaction. The Wolff-Kishner reduction is complementary to the Clemmensen reduction, base-labile molecules should be reduced by the Clemmensen method.
References
No references
Wurtz reaction

The coupling of alkyl halides upon treatment with a metal, e.g. elemental sodium, to yield symmetrical alkanes, is called the Wurtz reaction.
References
New trends in green chemistry, V.K. Ahluwalia, M. Kidwai, 2004, pg.no.132;
Organic chemistry, Bhupinder mehta, Manju mehta, 2005, pg. no.146;
Organic Chemistry, Dr. R.K Gupta & R. K. Amit, pg. No: 371
Organic reactions: Mechanisms with problems, Rajpal Tyagi, 2005, pg. no.493.
Organic Syntheses, Coll. Vol. 1, p.228 (1941); Vol. 9, p.54 (1929).
Organic Syntheses, Coll. Vol. 6, p.133 (1988); Vol. 51, p.55 (1971).
alpha-Bromination of oxocompounds

Alpha halogenation of aldehydes or ketones is an electrophil substitution reaction which can be either acid or base catalyzed and goes via the enol form of the aldehyde or ketone.
References
No references
alpha-Chlorination of oxocompounds

Alpha halogenation of aldehydes or ketones is an electrophil substitution reaction which can be either acid or base catalyzed and goes via the enol form of the aldehyde or ketone.
References
No references
alpha-Hydroxynitrile formation

This reaction is a nucleophilic addition of cyanide anion or a nitrile to an aldehyde or ketone followed by protonation of cyanide ion. Usually the cyanide source is potassium cyanide, sodium cyanide or trimethylsilyl cyanide. This nucleophilic addition is an equilibrium reaction, but with aliphatic carbonyl compounds equilibrium is in favor of the reaction products. Aqueous base usually decomposes cyanohydrins completely. The reaction with sterically hindered ketones, or ketones like ArCOR or ArCOAr give poor yields. In that case ketones can be converted to cyanohydrins by treatment with diethylaluminum cyanide or with trimethylsilanecarbonitrile (Me3SiCN) in the presence of a Lewis acid or base. With aromatic aldehydes the benzoin condensation competes. With alpha,beta-unsaturated aldehydes and ketones, 1,4-addition competes.
References
No references
alpha-Iodination of oxocompounds

Alpha halogenation of aldehydes or ketones is an electrophil substitution reaction which can be either acid or base catalyzed and goes via the enol form of the aldehyde or ketone.
References
No references
cross-Cannizzaro reaction

Aldehydes that have no alpha-hydrogen give the Cannizzaro reaction upon treatment with a strong base, e.g. an alkali hydroxide. In this disproportionation reaction one molecule is reduced to the corresponding alcohol, while a second one is oxidized to the carboxylic acid. The synthetic importance of the reaction is limited, because as a consequence of the disproportionation, the yield of the alcohol as well as the carboxylic acid is restricted to 50%. However good yields of alcohols can often be obtained when the reaction is carried out in the presence of equimolar amounts of formaldehyde. The formaldehyde is oxidized to formic acid and concomitantly reduces the other aldehyde to the desired alcohol. This variant is called the crossed Cannizzaro reaction. With aldehydes that do have alpha-hydrogens, the aldol reaction takes place preferentially.
References
No references
von Braun degradation of tertiary amines

Rosenmund von Braun degradation of tertiary amines cleaved by cyanogene bromide yields disubstituted cyanamide and alkyl halide. The reaction involves two nucleophilic substitutions via N-cyanoammonium bromide as intermediate. The first nucleophile is the tertiary amine, the second is the liberated bromide. Cyanide anion is not a nucleophile for aromatic systems, von Braun reaction is an exception.
References
No references
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