20.5 Hydride Reduction Reactions

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Reduction with Sodium Borohydride (NaBH4)

NaBH4 reduces ketones and aldehydes. It can also be used to reduce acid halides and anhydrides but LiAlH4 is more commonly used.

NaBH4 reduces ketones and aldehydes. It can also be used to reduce acid halides and anhydrides but LiAlH4 is more commonly used.

reduction of acid chloride with NaBH4
reduction of acid anhydride with NaBH4

Reduction with Lithium Aluminum Hydride (LiAlH4 aka LAH)

LiAlH4 reduces ketones, aldehydes, acid chlorides, acid anhydrides, esters, carboxylic acids, amides, nitriles (and others)

reduction of acid halide with LiAlH4
reduction of acid anhydride with LiAlH4
reduction of carboxylic acid with LiAlH4
reduction of carboxylic acid with BH3
reduction of ester with LiAlH4
reduction of amide with LiAlH4
reduction of nitrile with LiAlH4

Reduction with Lithium Tri-t-butoxy Aluminum Hydride

Lithium Tri-t-butoxy Aluminum Hydride reduces acid chlorides and acid anhydrides to aldehydes

reduction of acid chloride with tri-t-butoxyaluminum hydride
reduction of acid anhydride with tri-t-butoxyaluminum hydride

Reduction with DIBAH (aka DIBALH)

DIBAH reduces esters to aldehydes

reduction of ester with DIBAH