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Why are amides more resistant to hydrolysis than esters?

Answer 1

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Amides have a significant resonance contribution from a form that gives the nitrogen a positive charge.

This image shows a peptide bond (amide bond), but the idea is the same. This resonance form reduces the stability of the Amine as a leaving group. The resonance form may also make the carbonyl carbon less polarized, and therefore less susceptible to nucleophilic attack.

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Answer 2

Ryan Andrews

Amides are more resistant to hydrolysis than esters due to the presence of nitrogen in amides, which stabilizes the carbonyl carbon and reduces its electrophilicity compared to esters.

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Answer from HIX Tutor

When evaluating a one-sided limit, you need to be careful when a quantity is approaching zero since its sign is different depending on which way it is approaching zero from. Let us look at some examples.