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JEE Main levelSingle correct optionDifficulty 2 of 3hx027

Chlorobenzene does not give phenol with aqueous at room temperature. The best reason is that

  1. Athe carbon bearing is and sterically hindered by the ring
  2. B is a stronger base than , so it cannot leave
  3. Cthe benzene ring is non-polar, so cannot dissolve
  4. Dthe C-Cl bond has partial double bond character (resonance with the ring, carbon) and the phenyl cation is unstable

Answer: D

The lone pair on chlorine delocalises into the ring, giving the C-Cl bond partial double bond character, so it is shorter and stronger. The ring carbon is and the phenyl cation is unstable, so fails; backside attack is blocked by the ring, so fails. is a weaker base than , so (b) is wrong.
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