34.3.1—Reactions (reagents/conditions)

Ammonia reacts with an acyl chloride to make a primary amide; a primary amine makes an N-substituted amide. Both are room-temperature condensation reactions with HCl produced.

The nitrogen lone pair attacks the carbonyl carbon and chloride leaves. Use a second equivalent of ammonia or amine to remove the HCl in the overall equation.

CH₃COCl + 2NH₃ → CH₃CONH₂ + NH₄Cl; CH₃COCl + 2CH₃NH₂ → CH₃CONHCH₃ + CH₃NH₃Cl.

Do not count the second base molecule as part of the amide structure; it neutralises the HCl by-product.