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Toluene is treated with oleum to form a major product P. Compound P is heated with molten sodium hydroxide followed by acidification to yield compound Q. Finally, Q is distilled with zinc dust to produce compound R. Identify the structures of compounds Q and R respectively.

Options

  1. Ap -cresol and toluene
  2. Bm -cresol and toluene
  3. Cp -cresol and benzene
  4. Dbenzyl alcohol and toluene

Correct answer

A. p -cresol and toluene

Step-by-step solution

Toluene undergoes electrophilic aromatic substitution with oleum. The methyl group is an ortho/para directing group. Due to steric hindrance at the ortho position, the major product P is p -toluenesulfonic acid. Fusion of p -toluenesulfonic acid with molten NaOH followed by acidification replaces the sulfonate group ( - SO ₃ H ) with a hydroxyl group ( - OH ), yielding p -cresol (compound Q). Distillation of p -cresol with zinc dust reduces the phenolic - OH group, regenerating the aromatic hydrocarbon. The methyl

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