JEE Main 2021 · 27 August · evening · Single correct · +4 / −1

The correct structures of A and B formed in the following reactions 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

Reduce the nitro group first, then let the more nucleophilic NH₂ grab the one acetyl group.

  1. Find A. H₂/Pd in ethanol reduces only the -NO₂ group to -NH₂. The -OH is untouched, so A is p-aminophenol, HO-C₆H₄-NH₂.
  2. Compare nucleophiles. A now has two groups that can attack acetic anhydride, -NH₂ and -OH. Nitrogen is less electronegative than oxygen, so its lone pair is more available and -NH₂ is the stronger nucleophile.
  3. Only one equivalent. With just 1.0 eq of (CH₃CO)₂O, there is only enough reagent for one acylation, and the faster -NH₂ uses it up. The product is the amide HO-C₆H₄-NHCOCH₃, which is paracetamol.
  4. So. A is p-aminophenol and B is N-(4-hydroxyphenyl)acetamide, with the -OH still free. That is option (d).

The idea to keep. When a molecule has both -NH₂ and -OH and you add one equivalent of an acylating agent, the amine reacts first. You get the amide, not the ester.

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.