The reaction of an acyl chloride with aniline yields which functional group?

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Multiple Choice

The reaction of an acyl chloride with aniline yields which functional group?

Nucleophilic acyl substitution on a reactive acyl chloride is the key idea here. The carbonyl carbon of the acyl chloride is made highly electrophilic by the attached chlorine, so a nucleophilic nitrogen on aniline attacks it. This forms a tetrahedral intermediate, and the chloride leaves, yielding the amide with the structure R‑CO‑NHAr. The byproduct is HCl. An ester would require an oxygen nucleophile (like an alcohol) to form R‑CO‑OR, and an ether would come from an alkoxide adding to a carbonyl, not a nitrogen-containing nucleophile. An anhydride would involve another acyl group linking to the acyl chloride, which isn’t what happens in this direct amide-forming substitution.

Nucleophilic acyl substitution on a reactive acyl chloride is the key idea here. The carbonyl carbon of the acyl chloride is made highly electrophilic by the attached chlorine, so a nucleophilic nitrogen on aniline attacks it. This forms a tetrahedral intermediate, and the chloride leaves, yielding the amide with the structure R‑CO‑NHAr. The byproduct is HCl. An ester would require an oxygen nucleophile (like an alcohol) to form R‑CO‑OR, and an ether would come from an alkoxide adding to a carbonyl, not a nitrogen-containing nucleophile. An anhydride would involve another acyl group linking to the acyl chloride, which isn’t what happens in this direct amide-forming substitution.

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