NEET 2019 Odisha · ChemistryPrevious Year Question

The hydrolysis reaction (with aq. NaOH) that takes place at the slowest rate, among the following, is :

Answer: (A) (A) chloro-dimethylbenzene (aryl chloride) phenol derivative. In an aryl chloride the bond has partial double-bond character due to resonance of the halogen lone pair into the ring, and the carbon is hybridised, holding the halogen tightly.

  1. A.(A) chloro-dimethylbenzene (aryl chloride) phenol derivative
  2. B.(B) (ethyl chloride)
  3. C.(C) (allyl chloride)
  4. D.(D) (benzyl chloride)

Correct Answer

(A) (A) chloro-dimethylbenzene (aryl chloride) phenol derivative

Solution & Explanation

In an aryl chloride the bond has partial double-bond character due to resonance of the halogen lone pair into the ring, and the carbon is hybridised, holding the halogen tightly. Nucleophilic substitution/hydrolysis therefore requires drastic conditions and is the slowest. Ethyl chloride (, ), allyl chloride and benzyl chloride (both give resonance-stabilised carbocations / fast ) all hydrolyse readily, so the aryl chloride reacts slowest.

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