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(7 points) Explain why esters are more reactive towards nucleophilic acyl substitution compared to amides. Your answer should
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Answer #1

The first step of this reaction involves attack of nucleophile on carbonyl carbon. For this attack, rate is dependent of two factors:

Electrophilicty of carbon and steric hindrance: the main being the former one.

Clearly, the extent of electrophilicity decreases due to lone pair donation by oxygen and nitrogen in ester and amide respectively.

However, it is obvious that this donation would be stringer in case of N than O because N is less electronegative.

Hence Decrease in electrophilicity will be higher in amide and hence reaction will be less reactive towards nucleophilic acyl substitution.

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