Carboxylic Acid Derivatives 3/21

Reducing Esters

• esters reduced to primary alcohols using two equivalents of LiAlH4, NaBH4 is not strong enough

• NaBH4 is used to reduce an aldehyde or ketone to an alcohol in presence of an ester

• Reducing esters to aldehydes= use DIBALH, temperature-dependent

• If tried to do it at room temperature, the ester converts to the alcohol

Reducing Acid Halides

• Reduced to primary alcohols using lithium aluminum hydride and an acid wash

• first hydride forms aldehyde, second hydride forms the alcohol

Reduction of Amide

• using lithium aluminum hydride, you can make primary/secondary/tertiary amines

Reduction of Nitriles

• use LiAlH4 or H2/Pt

Synthesis of Nitriles