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Phenol reacts with Br ₂ in CS ₂ at 273 K to give a major product P. P reacts with aqueous NaOH followed by CH ₃ I to give Q. Q is heated with concentrated HI to give an aromatic product R and an aliphatic product S. Identify the structures of P, Q, and R.

Options

  1. AP is 2,4,6-tribromophenol; Q is 2,4,6-tribromoanisole; R is 2,4,6-tribromophenol
  2. BP is 4-bromophenol; Q is 4-bromoanisole; R is 4-bromophenol
  3. CP is 4-bromophenol; Q is 4-bromoanisole; R is 1-bromo-4-iodobenzene
  4. DP is 4-bromophenol; Q is 4-bromoanisole; R is 4-iodophenol

Correct answer

B. P is 4-bromophenol; Q is 4-bromoanisole; R is 4-bromophenol

Step-by-step solution

Phenol reacts with Br ₂ in a non-polar solvent ( CS ₂ ) at low temperature to undergo monohalogenation. The major product P is 4-bromophenol. 4-bromophenol reacts with aqueous NaOH to form sodium 4-bromophenoxide, which then undergoes Williamson ether synthesis with CH ₃ I to form 4-bromoanisole (Q). When 4-bromoanisole is heated with concentrated HI , the ether linkage is cleaved. Since the aryl-oxygen bond has partial double bond character due to resonance and is stronger, the cleavage occurs at the alkyl-oxygen

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