Nucleophilic Addition (Base)
A nucleophile adds directly to the carbonyl.
Nucleophilic Addition (Acid)
A protonated carbonyl is attacked by a nucleophile.
Hydrate Formation (Base)
Water adds under base to form a gem-diol.
Hydrate Formation (Acid)
Water adds under acid to form a gem-diol.
Acetal Formation
An aldehyde plus two alcohols gives an acetal.
Acetal Hydrolysis
Aqueous acid reverts an acetal to the carbonyl.
Imine Formation
A primary amine condenses to an imine.
Enamine Formation
A secondary amine condenses to an enamine.
Wolff–Kishner Reduction
A hydrazone reduces the carbonyl to CH2.
Dithioacetal Formation
Two thiols convert the carbonyl to a dithiane.
Dithioacetal Reduction
Raney nickel desulfurizes the dithiane to CH2.
Hydride Additions
NaBH4 or LAH reduce the carbonyl to an alcohol.
Grignard + Ketone
A Grignard reagent gives a tertiary alcohol.
Cyanohydrin Formation
HCN adds to give a cyanohydrin.
Wittig Olefination
An ylide converts the carbonyl into an alkene.
Baeyer–Villiger Oxidation
A peroxyacid inserts oxygen to form an ester.