17- Introduction to Carbonyl Chemistry

LAH (LiAlH4)

highly reactive and reduces most polar functional groups- all carbonyl compounds, nitriles, epoxides, halides, nitro, and others

LAH

special application: reduces carboxylic acids and esters to primary alcohols

LAH

special application: reduces amides to amines

DIBAL

less reactive than LAH and reduces most polar functional groups - all carbonyl compounds, nitriles, epoxides, halides, nitro, and others

DIBAL

special application: reduction of esters to aldehydes at a low temp

LTBA

slightly more reactive than NaBH4; special application: reduction of acid chlorides to aldehydes at a low temp

NaBH4

the mildest of the common reducing agents and reduces aldehydes and ketones without affecting less reactive groups (esters, acids, amides, nitriles)

NaBH4

its reaction with acid halides is not useful

reducing aldehydes and ketones to alcohols

typical application of NaBH4

reducing acetyl chlorides to aldehydes

typical application of LTBA

reducing esters to aldehydes

typical application of DIBAL

reducing aldehydes and ketones to alcohols

typical application of LAH (1)

reducing esters to primary alcohols

typical application of LAH (2)

reducing amides to amines

typical application of LAH (3)

reducing carboxylic acids to primary alcohols

typical application of LAH (4)