Which of the following derivatives of carboxylic acid is least reactive towards nucleophilic acyl substitution?
Correct answer: B. Acid amide
- A. Acid halide
- B. Acid amide
- C. Ester
- D. Acid anhydride
Explanation
The amide ion (NH2) is a very poor leaving group, making amides the least reactive of the common carboxylic acid derivatives. Their stability is also enhanced by resonance involving the nitrogen lone pair.
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About Carboxylic Acid Derivatives
Carboxylic acid derivatives include acid halides, acid anhydrides, esters and amides, formed by replacing the hydroxyl group of a carboxylic acid. Their nomenclature, structures, preparation, hydrolysis and relative reactivity are linked through nucleophilic acyl substitution, which differs from the nucleophilic addition reactions of aldehydes and ketones.
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