JEE Main 2024 · 30 January · evening · Single correct · +4 / −1
The products A and B formed in the following reaction scheme are respectively
- (a)
- (b)
- (c)
- (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.
- 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.
- 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.
- 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
- 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.