JEE Main 2021 · 17 March · evening · Single correct · +4 / −1

In the above reaction, the structural formula of (A), ''X'' and ''Y'' respectively 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 (b)

Solution

Chemistry ma’am · 3 steps

Ethanol swaps -N₂⁺ for H, and the -OCH₃ in anisole tells you where (A)'s oxygen sits.

  1. Find A. The product is anisole, so the -OCH₃ group was already on the ring of (A). Only the diazonium group leaves. That makes (A) p-methoxybenzenediazonium chloride, CH₃O-C₆H₄-N₂⁺ Cl⁻, which fits C₇H₇N₂OCl (C: 6 + 1, H: 4 + 3).
  2. What ethanol does. Ethanol is a mild reducing agent. It gives a hydrogen to the ring in place of N₂. In doing so ethanol is oxidised to acetaldehyde, CH₃CHO, and the chloride ion leaves as HCl.

    CH₃O-C₆H₄-N₂⁺Cl⁻ + CH₃CH₂OH → CH₃O-C₆H₅ + N₂ + CH₃CHO + HCl

  3. So. (A) is p-methoxybenzenediazonium chloride, X is CH₃CHO and Y is HCl. That is option (b).

The idea to keep. Diazonium salt plus ethanol (or H₃PO₂) means -N₂⁺ becomes -H. Ethanol goes to CH₃CHO, and the counter-ion leaves as its acid, here HCl.

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 2021.