Reactivity Order Esters
Mediumchemistry
Relative reactivity toward hydrolysis: acid chloride > ester > amide because amide is stabilized by:
Select the correct option:
Solution
Incorrect! Answer:
Resonance donation from nitrogen
- Nucleophilic Substitution: Hydrolysis involves the attack of a nucleophile (water or OH−) on the carbonyl carbon.
- Stabilization in Amides: In amides (R−CONH2), the Nitrogen atom has a lone pair of electrons.
- Internal Donation: This lone pair is strongly delocalized into the carbonyl group via resonance (N+=C−O−).
- Electronic Consequence: This delocalization effectively 'neutralizes' part of the partial positive charge on the Carbon, making it much less attractive to incoming nucleophiles.
- Reactivity: Acid chlorides have no such stabilizing resonance (poor 3p2˘0132p 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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About This Question
- Subject
- chemistry
- Chapter
- oxygen organics
- Topic
- reactivity order esters
- Difficulty
- Medium
- Year
- 2025
Solution
Correct Answer:
Resonance donation from nitrogen
- Nucleophilic Substitution: Hydrolysis involves the attack of a nucleophile (water or OH−) on the carbonyl carbon.
- Stabilization in Amides: In amides (R−CONH2), the Nitrogen atom has a lone pair of electrons.
- Internal Donation: This lone pair is strongly delocalized into the carbonyl group via resonance (N+=C−O−).
- Electronic Consequence: This delocalization effectively 'neutralizes' part of the partial positive charge on the Carbon, making it much less attractive to incoming nucleophiles.
- Reactivity: Acid chlorides have no such stabilizing resonance (poor 3p2˘0132p overlap), and Esters have moderate resonance from Oxygen. Thus, the resonance in amides makes them the most stable and least reactive toward hydrolysis.
This medium difficulty chemistry question is from the chapter oxygen organics, covering the topic of reactivity order esters. It appeared in the 2025 exam.
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