JEE Main 2021 · 31 August · evening · Single correct · +4 / −1

The major products A and B 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 (c)

Solution

Chemistry ma’am · 4 steps

Acetic anhydride caps the nitrogen first, and then the tamed ring takes just one bromine, at para.

  1. Acylation on nitrogen. The lone pair on the -NH₂ nitrogen is the most nucleophilic site in aniline, so (CH₃CO)₂O acylates the nitrogen, not the ring. A is acetanilide, C₆H₅NHCOCH₃.
  2. Activation is reduced. In -NHCOCH₃ the nitrogen lone pair is shared with the ring and also with the C=O group. The ring stays activated and ortho/para directing, but much less than in aniline, so it does not take three bromines the way aniline does.
  3. Para wins. With Br₂ in CH₃COOH at room temperature, only one bromine goes in. The bulky acetamido group blocks the ortho positions, so the major product is the para isomer.
  4. So. A is acetanilide and B is p-bromoacetanilide, 4-BrC₆H₄NHCOCH₃, which is option (c).

The idea to keep. Acetylating -NH₂ is the standard way to calm aniline down: you get monosubstitution, mostly para. The -NHCOCH₃ group is still an ortho/para director.

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.