Reactivity Order Esters

Question

Relative reactivity toward hydrolysis: acid chloride > ester > amide because amide is stabilized by:

RankGuru · Accepted Answer

1. **Nucleophilic Substitution**: Hydrolysis involves the attack of a nucleophile (water or $OH^-$) on the carbonyl carbon.
2. **Stabilization in Amides**: In amides ($R-CONH_2$), the Nitrogen atom has a lone pair of electrons.
3. **Internal Donation**: This lone pair is strongly delocalized into the carbonyl group via resonance ($N^+ = C - O^-$).
4. **Electronic Consequence**: This delocalization effectively 'neutralizes' part of the partial positive charge on the Carbon, making it much less attractive to incoming nucleophiles.
5. **Reactivity**: Acid chlorides have no such stabilizing resonance (poor $3p\u20132p$ overlap), and Esters have moderate resonance from Oxygen. Thus, the resonance in amides makes them the most stable and **least reactive** toward hydrolysis.

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Reactivity Order Esters

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