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Oxidations and reductions

A large part of synthesis consists in changing the oxidation state of a carbon: from alcohol to carbonyl, from nitro to amine, from ester to aldehyde. Modern oxidations and reductions make it possible to do so at a single group in a molecule that has many (chemoselectivity) and with control of the stereochemistry of the product.

This topic covers, functional group by functional group, the most useful reagents and their mechanisms: from hydrocarbons and halides to alcohols, amines, carbonyl compounds and carboxylic acid derivatives.

Syn dihydroxylation of cyclohexene with osmium tetroxide

Alkanes, alkenes, alkynes and arenes

 Reduction of an alkyl bromide with tributyltin hydride

Halogenated derivatives

 Swern oxidation of a primary alcohol to an aldehyde

Alcohols and phenols

 Reduction of nitrobenzene to aniline with hydrogen and palladium

Amines and anilines

 Baeyer–Villiger oxidation of cyclohexanone to ε-caprolactone

Aldehydes and ketones

 Reduction of an ester to an aldehyde with DIBAL-H at minus 78 degrees

Carboxylic acids and derivatives