Arrange the following acid derivatives in the decreasing order of their intrinsic reactivity towards nucleophilic acyl substitution ( mechanism): Acid chloride (I), Ester (II), Acid anhydride (III), A

Question

Arrange the following acid derivatives in the decreasing order of their intrinsic reactivity towards nucleophilic acyl substitution ($AN+DN$ mechanism): Acid chloride (I), Ester (II), Acid anhydride (III), Amide (IV).

Prashant Kotian · Accepted Answer

Correct answer: A. The reactivity of acid derivatives in the addition-elimination () mechanism heavily depends on the leaving group ability. Weaker bases are more stable and thus serve as better leaving groups. The basicity order of the leaving groups is . Therefore, the leaving group ability and overall reactivity order is Acid Chloride > Acid Anhydride > Ester > Amide.

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