Which reagents convert an acid chloride to a primary amide?

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Multiple Choice

Which reagents convert an acid chloride to a primary amide?

Amide formation from an acid chloride happens by nucleophilic acyl substitution: a nitrogen nucleophile attacks the carbonyl carbon, displacing chloride to give the amide. Ammonia is a good nitrogen nucleophile, so R-COCl + NH3 → R-CONH2 + HCl. In alcoholic ammonia, NH3 is present and the produced HCl is sequestered by the ammonia, helping drive the reaction to the primary amide. If an alcohol were used, the alcohol would attack and substitute the chloride to form an ester, not an amide. Water would hydrolyze the acid chloride to the carboxylic acid. A base alone doesn’t supply a nitrogen nucleophile, so it won’t form an amide.

Amide formation from an acid chloride happens by nucleophilic acyl substitution: a nitrogen nucleophile attacks the carbonyl carbon, displacing chloride to give the amide. Ammonia is a good nitrogen nucleophile, so R-COCl + NH3 → R-CONH2 + HCl. In alcoholic ammonia, NH3 is present and the produced HCl is sequestered by the ammonia, helping drive the reaction to the primary amide.

If an alcohol were used, the alcohol would attack and substitute the chloride to form an ester, not an amide. Water would hydrolyze the acid chloride to the carboxylic acid. A base alone doesn’t supply a nitrogen nucleophile, so it won’t form an amide.

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