Chapter 20: Carboxylic Acid Derivatives. Nucleophilic Acyl Substitution

Reduction of Nitriles
(for more detail see Chapter 22)

Reactions usually in Et₂O or THF followed by H₃O⁺work-up

Reaction type: Nucleophilic Addition

Summary

• The nitrile, RC≡N, gives the 1^o amine by conversion of the C≡N to -CH₂-NH₂
• Nitriles can be reduced by LiAlH₄ but NOT the less reactive NaBH₄
• Typical reagents :  LiAlH₄  / ether solvent followed by aqueous work-up.
• Catalytic hydrogenation (H₂ / catalyst) can also be used giving the same products.
• R may be either alkyl or aryl substituents.

© Dr. Ian Hunt, Department of Chemistry