How many of the following functional group classes typically undergo nucleophilic acyl substitution — Reaction Mechanism Chemistry Question
Question
How many of the following functional group classes typically undergo nucleophilic acyl substitution ($AN+DN$ mechanism) at a faster rate than a simple ester? List: Acid chloride, Acid anhydride, Amide, Carboxylate ion.
Answer: 2
💡 Solution & Explanation
The relative reactivity of acyl derivatives depends on their leaving groups: weaker bases are better leaving groups. The reactivity order is Acid Chloride > Acid Anhydride > Ester > Amide > Carboxylate ion. Comparing this to an ester, only Acid chlorides and Acid anhydrides react faster. Total count is 2.
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