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NEET CHEMISTRYMedium

Given below are two statements: Statement I: The product of the reaction of phenol with bromine depends on the nature of the solvent. Statement II: The reaction of phenol with bromine in CHCl3CHCl_3 gives a monosubstituted bromo derivative whereas the reaction of phenol with bromine water yields a trisubstituted bromo derivative of phenol.

In light of the above statements, choose the most appropriate answer from the options given below:

A

Statement I is correct and Statement II is incorrect

B

Statement I is incorrect and Statement II is correct

C

Both Statement I and Statement II are correct

D

Both Statement I and Statement II are incorrect

Step-by-Step Solution

The reaction of phenol with bromine is governed by the solvent's polarity, which affects the activation of the benzene ring:

  1. In non-polar or low polarity solvents (like CHCl3CHCl_3, CS2CS_2, or CCl4CCl_4) at low temperatures (273 K), the ionization of phenol is suppressed. The activation of the ring is moderate, resulting in monosubstitution. The products are a mixture of o-bromophenol (minor) and p-bromophenol (major).
  2. In aqueous solution (Bromine water), phenol ionizes to form the phenoxide ion. The phenoxide ion is a very strong activator towards electrophilic substitution because it releases more electron density into the ring. This leads to immediate trisubstitution at all available ortho and para positions, forming a white precipitate of 2,4,6-tribromophenol.
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