JEE Main 2022 · 26 July · morning · Single correct · +4 / −1

The correct stability order of the following diazonium salt is

JEE Main PYQ figure
  1. (a) (A)>(B)>(C)>(D)
  2. (b) (A)>(C)>(D)>(B)
  3. (c) (C)>(A)>(D)>(B)
  4. (d) (C)>(D)>(B)>(A)
Answer and solution

Answer (b) (A)>(C)>(D)>(B)

Solution

Chemistry ma’am · 3 steps

A diazonium ion is a cation, so electron-donating groups stabilise it and withdrawing groups do the opposite.

  1. Where the charge sits. The N₂⁺ group is positively charged and pulls electron density out of the benzene ring. A para group that pushes electrons into the ring spreads this positive charge out and stabilises the ion. A group that pulls electrons concentrates the charge and destabilises it.
    SaltPara groupEffect on the ringStability
    (A)OCH₃+R from the O lone pair, which outweighs its -Ihighest
    (C)Hnone, the referencesecond
    (D)CN-R and -Ithird
    (B)NO₂strongest -R and -Ilowest
  2. Nitro versus cyano. Both are withdrawing groups, but NO₂ pulls electrons more strongly than CN. So the nitro salt is the least stable of the two.
  3. So. The order is (A) > (C) > (D) > (B), which is option (b).

The idea to keep. For any cation on a benzene ring, rank by electron donation: +R donors such as OCH₃ stabilise most, H is the reference, and stronger withdrawers such as NO₂ destabilise most.

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 2022.