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JEE Main · 2022 · 26 Jul 2022 · Shift 1 · Alcohols Phenols and Ethers

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The difference in the reaction of phenol with bromine in chloroform and bromine in water medium is due to:
  1. (A)Hyperconjugation in substrate
  2. (B)Polarity of solvent✓ Correct
  3. (C)Free radical formation
  4. (D)Electromeric effect of the substrate

Answer: (B)

Solution

Phenol reacts with bromine differently in polar and non-polar solvents:
  • In CHCl₃ (non-polar): Br₂ is less ionized, reaction is slower, and mono-bromination occurs at the para position.
  • In H₂O (polar): Water ionizes phenol to phenoxide ion (more reactive) and increases the electrophilicity of Br₂ by polarization. This leads to rapid tribromination at ortho and para positions.

The key factor is solvent polarity, which affects both the reactivity of phenol (by ionization) and the electrophilicity of bromine.

Answer: (B) Polarity of solvent.

JEE Main · 2022 · 26 Jul 2022 · Shift 1 · Single correct option

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