JEE Main 2023 · 15 April · morning · Single correct · +4 / −1

Consider the following sequence of reactions:
The product ' B ' is

JEE Main PYQ figure
  1. (a)
    Option (a)
  2. (b)
    Option (b)
  3. (c)
    Option (c)
  4. (d)
    Option (d)
Answer and solution

Answer (a)

Solution

Chemistry ma’am · 4 steps

Aniline turns into a diazonium salt, which then couples at the para carbon of dimethylaniline.

  1. Make A. Aniline with NaNO₂ and acid at 0 to 5 °C undergoes diazotisation. A is benzenediazonium chloride, C₆H₅N₂⁺Cl⁻. The cold keeps this salt from decomposing.
  2. Find the electrophile. The terminal nitrogen of -N⁺≡N is a weak electrophile. It reacts only with very electron-rich rings, such as phenols and aromatic amines.
  3. Pick the site. In N,N-dimethylaniline, the -N(CH₃)₂ group pushes electron density onto the ring at the ortho and para positions. The bulky diazonium ion attacks the less crowded para carbon, and one H leaves as H⁺.

    C₆H₅N₂⁺Cl⁻ + C₆H₅N(CH₃)₂ → C₆H₅N=NC₆H₄N(CH₃)₂ + HCl

  4. So. B is 4-(N,N-dimethylamino)azobenzene, the yellow dye called butter yellow. Both nitrogens stay as -N=N⁻ joining the two rings, para to -N(CH₃)₂, which is option (a).

The idea to keep. In coupling, the diazonium ion keeps both nitrogens and adds as -N=N⁻ to the para carbon of an activated ring. Nothing is reduced and no N₂ is lost.

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 2023.