34.3.2—Reactions of amides

Hydrolysis breaks the amide C–N bond. Aqueous acid gives a carboxylic acid and an ammonium ion; aqueous alkali gives a carboxylate salt and ammonia or an amine.

Heating is normally required because the amide is resonance-stabilised. The reaction conditions determine whether the nitrogen product is protonated.

CH₃CONH₂ + H₂O/H⁺ → CH₃CO₂H + NH₄⁺; with aqueous NaOH the products are CH₃CO₂⁻Na⁺ and NH₃.

Do not write the same nitrogen product for acid and alkaline hydrolysis; the acid–base work-up changes its form.