Which reagents convert an acid chloride to a secondary amide?

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Multiple Choice

Which reagents convert an acid chloride to a secondary amide?

Acid chlorides are highly reactive toward nucleophilic substitution at the carbonyl carbon. To make an amide, a nitrogen nucleophile attacks the carbonyl, chloride leaves, and you end up with the acyl–nitrogen bond. The type of amide you get depends on the amine used. If you use a primary amine (R'NH2), the amide nitrogen ends up bonded to the carbonyl and to a single organic substituent from the amine, giving a secondary amide (R-CO-NH-R'). If you used ammonia, you’d form a primary amide (R-CO-NH2). Water would hydrolyze the acid chloride to the carboxylic acid, and an alcohol would give an ester, not an amide. So, to obtain a secondary amide, react the acid chloride with a primary amine (in alcohol).

Acid chlorides are highly reactive toward nucleophilic substitution at the carbonyl carbon. To make an amide, a nitrogen nucleophile attacks the carbonyl, chloride leaves, and you end up with the acyl–nitrogen bond. The type of amide you get depends on the amine used. If you use a primary amine (R'NH2), the amide nitrogen ends up bonded to the carbonyl and to a single organic substituent from the amine, giving a secondary amide (R-CO-NH-R'). If you used ammonia, you’d form a primary amide (R-CO-NH2). Water would hydrolyze the acid chloride to the carboxylic acid, and an alcohol would give an ester, not an amide. So, to obtain a secondary amide, react the acid chloride with a primary amine (in alcohol).

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