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JEE Advanced levelSingle correct optionDifficulty 3 of 3ap110

Benzene is treated with 2-chloropropane and anhydrous to give A. A is oxidised with air and then treated with dilute to give B and C. B is treated with excess bromine water to give D. D and C are, respectively,

  1. Abromobenzene and propanone
  2. B4-bromophenol and propanone
  3. C2,4,6-tribromophenol and propanal
  4. D2,4,6-tribromophenol and propanone

Answer: D

Friedel-Crafts alkylation gives cumene (A). Air oxidation gives cumene hydroperoxide, and acid-catalysed rearrangement gives phenol (B) and propanone (C). Phenol reacts with excess bromine water to give 2,4,6-tribromophenol (D).
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