Named Reactions

Alkanes 7
❖Wurtz Reaction ❖Ullmann Reaction
❖Fittig Reaction ❖Corey-House Synthesis
❖Kolbe Electrolysis
❖Wurtz-Fittig Reaction
❖Frankland Reaction
Wurtz Reaction
➢ Coupling reaction
➢ Alkyl radical, alkyl anion
➢ SN2
Fittig Reaction
Wurtz-Fittig Reaction
Frankland Reaction
➢ Intermediate is R2Zn
Ullmann Reaction
➢ Coupling reaction
➢ Organocopper intermediates (ArCu, ArCuX)
Corey-House Synthesis
➢ Lithium organocuprate-Gilman Reagent

Kolbe Electrolysis
Decarboxylative
dimerization
Anode Cathode
Alkenes & Alkynes 6
❖ Sabatier-Senderens Reaction ❖ Simmons-Smith Reaction
❖ Lindlar Reduction ❖ Ozonolysis Reaction
❖ Birch Reduction
❖ Diels-Alder Reaction
Sabatier-Senderens Reaction
➢ Heterogeneous catalytic hydrogenation

➢ Full reduction
Lindlar Reduction
Partial reduction with syn addition

Stereoselective reduction
Birch Reduction
➢ Partial reduction with anti addition

➢ Stereoselective reduction
➢ Radical anion intermediate
Diels-Alder Reaction
[4+2]-cycloaddition reaction between conjugated diene and

dienophile
Simmons-Smith Reaction
➢ Iodomethyl zinc iodide (ICH2ZnI) intermediate

➢ Carbenoid intermediate
➢ Cheletropic reaction (cycloaddition reaction)
Ozonolysis Reaction
➢ Addition & reductive
cleavage
➢ 1,3-cyclo addition
➢ Molozonide, ozonide
intermediates
Aromatic Hydrocarbons 3
❖ Friedel-Crafts Reaction
❖Gattermann Reaction
❖Gattermann -Koch Reaction

Friedel-Crafts Reaction
➢ Lewis acid catalyzed
electrophilic
substitution
➢ Acylium intermediate
in acylation
Gattermann Reaction ➢ Electrophilic
substitution
➢ Formimino chloride
and formimino cation
➢ Formyl chloride and
formyl cation
Gattermann -Koch Reaction

Organohalogens 4
❖Finkelstein Reaction
❖Sandmeyer Reaction
❖Gattermann Reaction
❖Balz-Schiemann Reaction
Finkelstein Reaction
➢ SN2 reaction
➢ Exchange halogen by another halogen
Sandmeyer Reaction
Radical nucleophilic
aromatic substitution
(SRNAr)
Gattermann Reaction
Balz-Schiemann Reaction
➢ Diazonium tetrafluoroborate intermediate

➢ Aryl cation intermediate
Alcohols, Phenols & Ethers 7
❖Reimer-Tiemann Reaction ❖ Azo Coupling Reaction
❖Kolbe-Schmitt Reaction ❖ Pinacol-Pinacolone

Rearrangement
❖Schotten-Baumann Reaction
❖ Williamson Synthesis
❖Fries Rearrangement
Reimer-Tiemann Reaction
➢ Ortho-formylation
➢ Dichlorocarbene
intermediate
Kolbe-Schmitt Reaction
➢ Carboxylation reaction
➢ Aromatic hydroxy acid
➢ Nucleophilic addition
Schotten-Baumann Reaction
Conversion of acid
chlorides to esters
Fries Rearrangement
Acylium Carbocation
intermediate
Electrophilic aromatic
substitution
> 100 oC RT
Azo Coupling Reaction
Electrophilic
substitution
Reaction
Pinacol-Pinacolone Rearrangement
➢ 1,2 - diol to carbonyl

➢ 1,2- rearrangement
➢ Carbocation intermediate
Williamson Synthesis
SN2 reaction of alkoxide with 1o alkyl halide

Aldehydes & Ketones 19
❖Étard Reaction ❖ Cannizzaro Reaction
❖ Claisen-Schmidt Condensation
❖Rosenmund Reaction
❖ Perkin Reaction
❖Stephen’s Reduction
❖ Benzoin Condensation
❖Wacker Process
❖ Oxo Process
❖ Aldol Condensation
Aldehydes & Ketones
❖ Reformatsky Reaction ❖ MPV Reduction
❖ Knoevenagel Reaction ❖ Oppenauer’s Oxidation
❖ Baeyer Villiger Reaction ❖ Wittig Reaction
❖ Clemmensen Reduction ❖ Michael Addition Reaction
❖ Wolf-Kishner Reduction
Étard Reaction
➢ Partial oxidation
Rosenmund Reaction
➢ Hydrogenolysis
➢ Thiourea as poison
➢ Formaldehyde can’t be prepared
Stephen’s Reduction
➢ Iminium salt intermediate

Wacker Process
Homogeneous catalysis reaction

Oxo Process
➢ Hydroformylation reaction
➢ Synthesis gas
➢ Homogeneous catalysis
➢ Formylation at low substituted carbon
Aldol Condensation Reaction
Cannizzaro Reaction
➢ Disproportionation reaction
➢ Reaction follows third order kinetics
Claisen-Schmidt Condensation
Perkin Reaction
Aldol condensation between aromatic aldehyde and

acid anhydride
Reformatsky Reaction
Organozinc intermediate-Reformatsky enolate

Knoevenagel Reaction
Modification of Aldol condensation between carbonyl

and active hydrogen compound
Benzoin Condensation Reaction
➢ Addition reaction between two aromatic

aldehydes in presence of cyanide
➢ Acyloin
Baeyer Villiger Reaction
Clemmensen Reduction
Zinc carbenoid intermediates

Wolf-Kishner Reduction
Hydrazone & diimide anion intermediates

Meerwein-Pondorf-Verley (MPV) Reduction
Oppenauer’s Oxidation
Wittig Reaction
➢ Olefination reaction
➢ Triphenyl phosphonium ylide
➢ Betaine & oxaphosphetane intermediates
Michael Addition Reaction
Conjugate addition reaction between carbanion

and alpha beta unsaturated carbonyl
Carboxylic acids & its derivatives 6
❖ Huns-Diecker Reaction ❖ Tischenko Reaction

❖ Schmidt Reaction ❖ Claisen Condensation
❖ Arndt-Eistert Reaction
❖ Hell-Volhard-Zelinksy Reaction
Hunsdiecker Reaction
➢ Decarboxylation & halogenation

➢ Acyl hypohalite and alkyl free radical
Arndt-Eistert Reaction
➢ Homologation of carboxylic acid

➢ Acid chloride
➢ Wolff Rearrangement (Conversion of
diazoketone to ketene)
Schmidt Reaction
Similar to Curtius rearrangement
Similar to Baeyer-Villiger oxidation

Hell-Volhard-Zelinksy (HVZ) Reaction
➢ Halogenation of carboxylic acids

➢ Used in Strecker synthesis
Tischenko Reaction
Claisen Condensation
➢ Alpha hydrogen containing ester

➢ Beta keto ester
Nitrogen compounds 11
❖ Hofmann Mustard Oil Reaction ❖ Hofmann Elimination

❖ Nef Reaction ❖ Cope Elimination
❖ Mannich Reaction ❖ Diazotization Reaction
❖ Gabriel Phthalimide Synthesis
Nitrogen compounds
❖ Beckmann Rearrangement
❖ Curtius Rearrangement
❖ Lossen Rearrangement
❖ Hofmann Rearrangement
Hofmann Mustard Oil Reaction
Nef Reaction
Acid hydrolysis of salts of 1o or
2o nitroalkane
Mannich Reaction
➢ Amino alkylation of acidic proton

➢ Iminium ion intermediate
Gabriel Phthalimide Synthesis
Hofmann Elimination
Cope Elimination
Diazotization Reaction
Beckmann Rearrangement
Nitrilium ion, imidate intermediate

Curtius Rearrangement
Lossen Rearrangement
Hofmann Rearrangement (Hofmann Bromide Reaction)

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Alkanes 7

❖Wurtz Reaction ❖Ullmann Reaction

❖Fittig Reaction ❖Corey-House Synthesis

➢ Lithium organocuprate-Gilman Reagent

❖ Sabatier-Senderens Reaction ❖ Simmons-Smith Reaction

❖ Lindlar Reduction ❖ Ozonolysis Reaction

➢ Heterogeneous catalytic hydrogenation

Partial reduction with syn addition

➢ Partial reduction with anti addition

[4+2]-cycloaddition reaction between conjugated diene and

➢ Iodomethyl zinc iodide (ICH2ZnI) intermediate

❖Gattermann -Koch Reaction

Gattermann -Koch Reaction

➢ Diazonium tetrafluoroborate intermediate

❖Reimer-Tiemann Reaction ❖ Azo Coupling Reaction

❖Kolbe-Schmitt Reaction ❖ Pinacol-Pinacolone

➢ 1,2 - diol to carbonyl

SN2 reaction of alkoxide with 1o alkyl halide

➢ Iminium salt intermediate

Homogeneous catalysis reaction

Aldol condensation between aromatic aldehyde and

Organozinc intermediate-Reformatsky enolate

Modification of Aldol condensation between carbonyl

➢ Addition reaction between two aromatic

Zinc carbenoid intermediates

Hydrazone & diimide anion intermediates

Conjugate addition reaction between carbanion

❖ Huns-Diecker Reaction ❖ Tischenko Reaction

➢ Decarboxylation & halogenation

➢ Homologation of carboxylic acid

Similar to Baeyer-Villiger oxidation

➢ Halogenation of carboxylic acids

➢ Alpha hydrogen containing ester

❖ Hofmann Mustard Oil Reaction ❖ Hofmann Elimination

➢ Amino alkylation of acidic proton

Nitrilium ion, imidate intermediate

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