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The products P1, P2, P3 and P4 of the following reactions are

(i) \(\mathrm{C_{6}H_{5}SO_{3}Na \xrightarrow{NaOH,\ H^{+}} P_{1}}\)
(ii) \(\mathrm{C_{6}H_{5}OH \xrightarrow{CO_{2} / NaOH / H^{+}} P_{2}}\)
(iii) \(\mathrm{C_{6}H_{5}OH \xrightarrow{NaOH,\ CH_{3}Cl} P_{3}}\)
(iv) \(\mathrm{o\text{-}HOC_{6}H_{4}COOH \xrightarrow{(CH_{3}CO)_{2}O,\ H^{+}} P_{4}}\)

  • A.\(P_{1}\) = Phenol, \(P_{2}\)= Salicylaldehyde, \(P_{3}\) = Cyclohexanol, \(P_{4}\) = Phenyl acetate,
  • B.\(P_{1}\) = Benzene, \(P_{2}\) = Salicylic acid, \(P_{3}\) = Cyclohexanol, \(P_{4}\)= Phenyl acetate,
  • C.\(P_{1}\) = Phenol, \(P_{2}\) = Salicylic acid, \(P_{3}\) = Anisole, \(P_{4}\) = Aspirin,
  • D.\(P_{1}\) = Phenol, \(P_{2}\) = Salicylic acid, \(P_{3}\) = Anisole, \(P_{4}\) = Phenyl acetate,
  • E.\(P_{1}\) = Cyclohexanol, \(P_{2}\) = Salicylic acid, \(P_{3}\)= Phenol, \(P_{4}\) = Aspirin,

Answer: C

The products are P1 = Phenol, P2 = Salicylic acid, P3 = Anisole, P4 = Aspirin.

  1. Sodium benzenesulphonate fused with NaOH gives sodium phenoxide, and acid releases phenol.
  2. Kolbe's reaction: sodium phenoxide with CO2 under pressure, then acid, gives salicylic acid (2-hydroxybenzoic acid).
  3. Williamson synthesis: phenoxide with methyl chloride gives methyl phenyl ether, anisole.
  4. Acetylation of the phenolic OH of salicylic acid with acetic anhydride gives acetylsalicylic acid, aspirin.

Salicylaldehyde comes from the Reimer-Tiemann reaction (chloroform and alkali), not from CO2. Cyclohexanol would need hydrogenation of the ring, which none of these reagents does. Phenyl acetate is the acetate of phenol itself, but the substrate in (iv) is salicylic acid, so its acetate is aspirin.

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