JEE Main 2024 · 30 January · evening · Single correct · +4 / −1

The products A and B formed in the following reaction scheme are respectively

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

Answer (b)

Solution

Chemistry ma’am · 4 steps

Nitro reduces to aniline, aniline becomes a diazonium salt, and phenol grabs it at the para position.

  1. Nitrate, then reduce. Concentrated HNO₃/H₂SO₄ at 323 to 333 K puts one -NO₂ group on benzene to give nitrobenzene. Sn/HCl then reduces -NO₂ to -NH₂, so A is aniline, C₆H₅NH₂.
  2. Diazotise in the cold. NaNO₂ + HCl makes nitrous acid, which turns aniline into benzenediazonium chloride, C₆H₅N₂⁺Cl⁻. The temperature is kept at 273 to 278 K because this salt decomposes when warm.
  3. Couple with phenol. The diazonium ion is a weak electrophile. It attacks the activated phenol ring at the para position, the least hindered site, and the -N=N⁻ bridge stays in the product.

    C₆H₅N₂⁺Cl⁻ + C₆H₅OH → C₆H₅-N=N-C₆H₄-OH (p) + HCl

  4. So. B is p-hydroxyazobenzene, the orange azo dye. Aniline and p-hydroxyazobenzene is option (b).

The idea to keep. In azo coupling the diazonium nitrogens are kept, giving an -N=N⁻ link, and the attack goes to the para position of phenol or aniline. Ortho coupling happens only when para is blocked.

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 2024.