An acid chloride treated with a tertiary amine yields which product?

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Multiple Choice

An acid chloride treated with a tertiary amine yields which product?

An acid chloride behaves as an acylating agent, and a nucleophilic amine nitrogen attacks the carbonyl carbon to form an amide. Since the amine is tertiary, its nitrogen has no N–H bonds. After acylation, the nitrogen ends up bonded to the carbonyl carbon and retains two carbon substituents from the original tertiary amine, giving a tertiary amide. A proton transfer typically occurs with the generated HCl, which is often sequestered by excess base to form a salt, but the organic product is the tertiary amide. The other possibilities would require an N–H on the amide nitrogen (primary or secondary amide) or a different pathway (like hydrolysis to a carboxylic acid), which aren’t what happens under straightforward acylation with an acid chloride.

An acid chloride behaves as an acylating agent, and a nucleophilic amine nitrogen attacks the carbonyl carbon to form an amide. Since the amine is tertiary, its nitrogen has no N–H bonds. After acylation, the nitrogen ends up bonded to the carbonyl carbon and retains two carbon substituents from the original tertiary amine, giving a tertiary amide. A proton transfer typically occurs with the generated HCl, which is often sequestered by excess base to form a salt, but the organic product is the tertiary amide. The other possibilities would require an N–H on the amide nitrogen (primary or secondary amide) or a different pathway (like hydrolysis to a carboxylic acid), which aren’t what happens under straightforward acylation with an acid chloride.

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