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NEET CHEMISTRYAlcohols, Phenols and EthersMedium

Question

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.

Exam Context & Concepts Covered

This question aligns with the NEET CHEMISTRY syllabus, specifically targeting concepts from Alcohols, Phenols and Ethers. Mastering this topic is crucial for scoring well in the upcoming medical entrance examinations. Solving conceptually related problems will help you understand the nuances of these concepts and improve your problem-solving speed.

CHEMISTRYAlcohols, Phenols and Ethersstatementsstatementproductreactionphenol

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