JEE Main 2021 · 25 July · evening · Single correct · +4 / −1

C₆H₅NO₂ →(Sn + HCl) “A” →(C₆H₅N(⊕)₂Cl(⊖)) P
Consider the above reaction, the product "P" is :

  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 · 4 steps

Nitro goes to amine first, then the diazonium ion grabs the para carbon of aniline to make a yellow azo dye.

  1. Find A. Sn + HCl reduces the nitro group fully to an amino group. So nitrobenzene becomes aniline, C₆H₅NH₂, which is A.
  2. Coupling with aniline. The benzenediazonium ion is a weak electrophile, and it attacks the activated ring of aniline. The -NH₂ group directs it ortho and para, and the bulky C₆H₅N₂⁺ group prefers the free, uncrowded para carbon.

    C₆H₅N₂⁺Cl⁻ + C₆H₅NH₂ →(H⁺) C₆H₅-N=N-C₆H₄-NH₂ (p) + HCl

  3. Why it is yellow. The -N=N⁻ link joins two benzene rings into one long conjugated system. That system absorbs blue light, so the compound looks yellow. This is p-aminoazobenzene, the dye called aniline yellow.
  4. So. P is p-aminoazobenzene, option (b).

The idea to keep. Diazonium salts couple with phenols and anilines at the para position to give coloured azo compounds. Look for the -N=N⁻ bridge with the activating group para to it.

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.