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Alcohols Phenols and Ethers question

2011 · Shift 0 · Q16
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Alcohols Phenols and Ethers question

2011 · Shift 0 · Q16

JEE MainChemistryAlcohols Phenols and EthersMCQ+4 / −1
Phenol is heated with a solution of mixture of KBrKBrKBr and KBrO3KBrO_3KBrO3​. The major product obtained in the above reaction is
  1. A
    3-Bromophenol
  2. B
    4-Bromophenol
  3. C
    2, 4, 6- Tribromophenol
  4. D
    2-Bromophenol
View written solutionFree

Correct answer: C

  1. Identify the reagent generated in situ

A mixture of KBrKBrKBr and KBrO3KBrO_3KBrO3​ in solution generates bromine under acidic conditions:

BrO3−+5Br−+6H+→3Br2+3H2OBrO_3^- + 5Br^- + 6H^+ \rightarrow 3Br_2 + 3H_2OBrO3−​+5Br−+6H+→3Br2​+3H2​O

So effectively, phenol is being treated with bromine water / brominating conditions.

  1. Reactivity of phenol toward electrophilic substitution

The −OH-OH−OH group in phenol is strongly activating due to resonance donation of lone pair electrons into the benzene ring. Therefore:

  • the ring becomes highly reactive toward electrophilic substitution,
  • substitution occurs mainly at the ortho and para positions.

Because phenol is very strongly activating, bromination does not usually stop at mono-bromination under such conditions.

  1. Effect of bromine on phenol

When phenol reacts with bromine water, it undergoes rapid multiple substitution to give:

Phenol→Br22,4,6-tribromophenol\text{Phenol} \xrightarrow{Br_2} \text{2,4,6-tribromophenol}PhenolBr2​​2,4,6-tribromophenol

The three activated positions (2,4,62,4,62,4,6) all get brominated.

  1. Evaluate the options
  • A: 3-Bromophenol — incorrect, meta substitution is not favored.
  • B: 4-Bromophenol — incorrect as major product under these conditions because bromination continues further.
  • C: 2,4,6-Tribromophenol — correct.
  • D: 2-Bromophenol — incorrect as major product for the same reason.
  1. Final answer

The major product is:

2,4,6-Tribromophenol\boxed{\text{2,4,6-Tribromophenol}}2,4,6-Tribromophenol​

So, the correct option is C.

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