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JEE Advanced2022Paper 1CHEM-II
Q.

Considering the following reaction sequence,

the correct option(s) is(are)

  1. A
  2. B
  3. C
  4. D
Solution

The starting material p-nitrotoluene is first reduced by P (either H/Pd in ethanol or Sn/HCl, both reduce –NO to –NH) to give Q = p-toluidine (4-methylaniline). So options (A) and (B) for P are both viable, but (D) misidentifies Q as 4-nitrobenzoic acid.

Diazotisation by R (NaNO/HCl or HNO) at low temperature gives S = p-tolyl diazonium chloride. Both (A) and (B) describe valid choices for R.

Hydrolysis of S with warm HO gives T = p-cresol (4-methylphenol).

Conversion of S to benzoic acid by U requires two operations: replacement of the diazonium group by H (using HPO or CHCHOH), giving toluene, and then oxidation of the methyl group with alkaline KMnO followed by acidification, giving benzoic acid. Both forms of U in (A) and (C) are correct.

Therefore options (A), (B) and (C) all describe valid steps. Option (D) is wrong because Q in this sequence is the amine, not the carboxylic acid.

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