JEE Main 2022 · 26 June · evening · Single correct · +4 / −1

The final product 'C' in the following series of reactions

JEE Main PYQ figure
  1. (a)
    Option (a)
  2. (b)
    Option (b)
  3. (c)
    Option (c)
  4. (d)
    Option (d)
Answer and solution

Answer (c)

Solution

Chemistry ma’am · 4 steps

Nitro to amine, amine to diazonium, then the diazonium couples at C1 of β-naphthol, right next to the OH.

  1. Reduction gives A. Sn/HCl reduces the nitro group to an amino group. So A is aniline, C₆H₅NH₂.
  2. Diazotisation gives B. NaNO₂ and HCl generate nitrous acid, which converts aniline at 0 to 5 °C into benzenediazonium chloride. So B is C₆H₅N₂⁺Cl⁻.

    C₆H₅NO₂ →(Sn/HCl) C₆H₅NH₂ →(NaNO₂/HCl, 0-5 °C) C₆H₅N₂⁺Cl⁻

  3. Coupling gives C. β-Naphthol has its OH at C2. In NaOH it becomes the naphthoxide ion, a strong ortho/para director. The weakly electrophilic diazonium ion attacks C1, the α-position ortho to -O⁻. Attack at C1 keeps the other benzene ring fully aromatic in the intermediate, so C1 wins over C3.
  4. So. C is 1-phenylazo-2-naphthol, the orange-red dye with -N=N-C₆H₅ on C1 and OH on C2. That is option (c).

The idea to keep. Diazonium ions are weak electrophiles, so they only attack strongly activated rings. With β-naphthol, coupling always goes to C1, the α-carbon right beside the OH, and never to the other ring.

Answer from the NTA final answer key. Solution by PrepWiser.

Study Amines & Diazonium Salts

Asked about 170 times in JEE Main since 2020. This question is from 2022.