Phenol reacts with bromine WATER (aqueous $\mathrm{Br_2}$) at room temperature to give
Amonobromophenol
B2,4,6-tribromophenol
Cbromobenzene
Dphenol stays unreacted
Answer & Solution
Correct answer: B. 2,4,6-tribromophenol
1. Your syllabus (Phenol reactions — electrophilic substitution): phenol is HIGHLY ACTIVATED toward electrophilic substitution because the $\mathrm{-OH}$ donates electrons strongly into the ring (resonance + inductive ortho/para director).
2. With $\mathrm{Br_2}$ in WATER, the polar medium ENHANCES the reactivity further (because the phenoxide form $\mathrm{C_6H_5O^-}$ is even more reactive than phenol itself).
3. Multiple bromine atoms add — all three ortho/para positions get brominated, giving 2,4,6-TRIBROMOPHENOL as a WHITE PRECIPITATE.
4. In contrast: with $\mathrm{Br_2}$ in $\mathrm{CS_2}$ (non-polar solvent), the reaction is milder and gives mainly monobrominated product (ortho or para).
5. Option A is the $\mathrm{CS_2}$-medium product (selectivity by reagent/solvent). Option C is what would form with $\mathrm{C_6H_6}$ and Fe catalyst, NOT phenol. Option D contradicts phenol's very high reactivity.
_Source: syllabus Chemistry Part 2, Ch 7, §7.7 (Phenol — bromination), p. 18._
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