Q31 / 150 · MHT CET 2025 (22 Apr Shift 1) · Chemistry

Phenol on reaction with aqueous solution of bromine gives

  • A
    o-Bromophenol
  • B
    m-Bromophenol
  • C
    p-Bromophenol
  • Correct answer
    D
    2,4,6-tribromophenol

Solution

The electrophilic aromatic substitution of phenol with aqueous bromine proceeds vigorously due to the strong activating nature of the hydroxyl group, which directs substitution to ortho and para positions.

Bromine water acts as both a source of electrophilic $Br^+$ and a polar protic solvent, enhancing electrophilicity and stabilizing reaction intermediates. All three activated positions—two ortho and one para—undergo substitution, yielding 2,4,6-tribromophenol as a white precipitate.

$C_6H_5OH + 3Br_2(aq) \rightarrow C_6H_2Br_3OH + 3HBr$

Final answer: $\boxed{D}$

Hence, the correct answer is option: 'D'.

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