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Multiple Choice

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

Acid chlorides react with amines through acyl substitution: the lone pair on nitrogen attacks the carbonyl carbon, chloride leaves, and the amide forms with the nitrogen bearing the substituents that came from the amine. With a secondary amine, nitrogen already has two carbon substituents; after amidation it keeps those two substituents plus the carbonyl, giving a tertiary amide (R-CO-NR2). No hydrogen remains on nitrogen in this product, hence it’s not a secondary or primary amide. A carboxylic acid would arise only from hydrolysis or different conditions, not from direct reaction with the amine.

Acid chlorides react with amines through acyl substitution: the lone pair on nitrogen attacks the carbonyl carbon, chloride leaves, and the amide forms with the nitrogen bearing the substituents that came from the amine. With a secondary amine, nitrogen already has two carbon substituents; after amidation it keeps those two substituents plus the carbonyl, giving a tertiary amide (R-CO-NR2). No hydrogen remains on nitrogen in this product, hence it’s not a secondary or primary amide. A carboxylic acid would arise only from hydrolysis or different conditions, not from direct reaction with the amine.