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JEE Main 2025 Apr 2 Shift 1, Chemistry Q19: Carboxylic Acid Derivatives

JEE Main2025Apr 2, Shift 1Chemistry
Q.

Consider the following molecules :

The correct order of rate of hydrolysis is :

  1. A

  2. B

  3. C

  4. D

Solution

For nucleophilic acyl substitution, the rate is governed by how good a leaving group the X attached to the acyl carbon is. Ranking leaving groups:

(acid chloride) (anhydride) (ester) (amide)

Equivalently, resonance donation from X into the carbonyl reduces its electrophilicity in the reverse order:

Amide (strong N C=O resonance) ester anhydride acid chloride (weakest donor) — meaning the acid chloride is the most reactive electrophile.

Therefore the hydrolysis order is:

Option (4) is correct.

Concept behind this question

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