JEE Main 2025 · 22 January · morning · Single correct · +4 / −1
The products formed in the following reaction sequence are :
- (a)
- (b)
- (c)
- (d)
Answer and solution
Answer (d)
Solution
Chemistry ma’am · 4 steps
Ethanol does not put an OEt on the ring here. It swaps N₂⁺ for H and becomes acetaldehyde.
- Bromination. The -NO₂ group deactivates the ring and directs to the meta position. Br₂ in acetic acid gives meta-bromonitrobenzene.
- Reduce, then diazotise. Sn and HCl reduce -NO₂ to -NH₂, giving meta-bromoaniline. Then NaNO₂ and HCl at 273 K turn it into meta-bromobenzenediazonium chloride.
- Ethanol as reducer. Ethanol reduces the diazonium salt. The -N₂⁺ group is replaced by H and nitrogen gas escapes. Ethanol loses two hydrogens and is oxidised to acetaldehyde.
BrC₆H₄N₂⁺Cl⁻ + CH₃CH₂OH → C₆H₅Br + N₂ + CH₃CHO + HCl
- So. With the nitrogen gone, only Br is left on the ring, so its position no longer matters. A is bromobenzene and B is CH₃CHO, which is option (d).
The idea to keep. Diazonium salt with ethanol or H₃PO₂ means the -N₂⁺ group is replaced by H. Ethanol stops at acetaldehyde. Only warm water gives a phenol.
Answer from the NTA final answer key. Solution by PrepWiser.