Question

Provide a detailed, stepwise mechanism for the reaction of benzoyl chloride with methyl amine, using curved arrows to show electron flow.

Answer 1

Benzoyl chloride when reacts with methyl amine then N-methyl benzamide and hydrochloric acid (HCl) is formed. But HCl immediately reacts with another molecule of the amine (methyl amine) and gives an salt of amine (methyl ammonium chloride).

In this reaction, first the nucleophilic addition of the methyl amine with benzoyl chloride gives a tetrahedral intermediate. Then the leaving group elimination of Cl^- and followed by the deprotonation give the amide N-methyl benzamide.

Protonation of methyl amine gives methyl ammonium chloride as follows