33.3.2—Reactions of acyl chlorides

Acyl chlorides undergo nucleophilic acyl substitution. Water gives a carboxylic acid, an alcohol gives an ester, ammonia gives a primary amide, and a primary amine gives a substituted amide; HCl is formed.

The nucleophile attacks the carbonyl carbon, then chloride leaves. Match the nucleophile to the product family before writing the equation.

CH₃COCl + H₂O → CH₃CO₂H + HCl; CH₃COCl + NH₃ → CH₃CONH₂ + HCl.

Do not write an alkene addition product or omit HCl when balancing the overall reaction.