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The product of reaction of phenol with bromine water (excess) is:

  1. (a) o-bromophenol
  2. (b) p-bromophenol
  3. (c) 2,4,6-tribromophenol
  4. (d) m-bromophenol
Answer and solution

Answer (c) 2,4,6-tribromophenol

Solution

Chemistry ma’am · 4 steps

In water, phenol's OH makes the ring so reactive that every free ortho and para spot takes a bromine.

  1. Strong activation. The -OH group pushes electron density into the ring through resonance. The extra electron density sits at the two ortho positions and the para position.
  2. Role of water. Water is a polar solvent, so it helps phenol ionise partly to the phenoxide ion, which is even more electron-rich. Water also polarises Br₂, so no Lewis acid catalyst is needed.
  3. No stopping. With excess bromine water, substitution does not stop after one bromine. All three activated positions (2, 4 and 6) are brominated, and a white precipitate forms.

    C₆H₅OH + 3Br₂ →(H₂O) C₆H₂Br₃OH v + 3HBr

  4. So. The product is 2,4,6-tribromophenol, option (c).

The idea to keep. Phenol with bromine water gives the white 2,4,6-tribromo precipitate. You get mono-bromophenols only in a non-polar solvent like CS₂ or CHCl₃ at low temperature.

Answer from the NTA final answer key. Solution by PrepWiser.

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