Reactivity of carboxylic acid derivatives
Which carboxylic acid derivative is most reactive toward nucleophilic acyl substitution?
Answer A: explanation for every choice
A
Correct. Chloride is the best leaving group of these.
B
Anhydrides are second most reactive.
C
Esters are less reactive, since alkoxide is a poorer leaving group.
D
Amides are least reactive, stabilized by strong nitrogen resonance.
TakeawayAcid chloride > anhydride > ester > amide. A better leaving group means more reactive.
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Reviewed 2026-11-05 by a medical student. Spot an error? Report it with question ID cp52.