JEE Main · 2022 · 27 Jul 2022 · Shift 2 · Compounds Containing Nitrogen

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An organic compound 'A' contains nitrogen and chlorine. It dissolves readily in water to give a solution that turns litmus red. Titration of compound 'A' with standard base indicates that the molecular weight of 'A' is . When a sample of 'A' is treated with aq. NaOH, a liquid separates which contains N but not Cl. Treatment of the obtained liquid with nitrous acid followed by phenol gives orange precipitate. The compound 'A' is:
  1. (A)(see structure)
  2. (B)(see structure)
  3. (C)(see structure)
  4. (D)(see structure)
    ✓ Correct

Answer: (D)

Solution

The compound A is anilinium chloride (C₆H₅NH₃⁺Cl⁻). Key observations:
  1. Molecular weight ≈ 131 (matches C₆H₅NH₃Cl: 93.5 + 36.5 = 130)
  2. Dissolves in water and turns litmus red → acidic salt
  3. Treatment with NaOH releases aniline (contains N, no Cl)
  4. Aniline + HNO₂ → benzenediazonium salt
  5. Diazonium salt + phenol → orange azo dye (coupling reaction)

This confirms compound A is anilinium chloride, shown in option (D).

JEE Main · 2022 · 27 Jul 2022 · Shift 2 · Single correct option

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