JEE Main 2025 · 22 January · morning · Single correct · +4 / −1

The products formed in the following reaction sequence are :

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

  1. Bromination. The -NO₂ group deactivates the ring and directs to the meta position. Br₂ in acetic acid gives meta-bromonitrobenzene.
  2. 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.
  3. 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

  4. 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.

Study Amines & Diazonium Salts

Asked about 170 times in JEE Main since 2020. This question is from 2025.