JEE Main 2022 · 26 June · evening · Single correct · +4 / −1
The final product 'C' in the following series of reactions
- (a)
- (b)
- (c)
- (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.
- Reduction gives A. Sn/HCl reduces the nitro group to an amino group. So A is aniline, C₆H₅NH₂.
- 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⁻
- 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.
- 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.