JEE Main 2022 · 29 July · morning · Single correct · +4 / −1

Which among the following represent reagent 'A'?

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 · 3 steps

NaOH plus an orange-red dye points straight to 2-naphthol, the classic coupling partner in alkali.

  1. Read the medium. Benzenediazonium chloride is a weak electrophile, so it couples only with a strongly activated ring. NaOH turns a phenol or naphthol into its phenoxide ion. The O⁻ group activates the ring strongly enough for coupling. Amines are coupled in a mildly acidic medium instead.
  2. Where it couples. In 2-naphthol, the diazonium ion attacks C-1, the position right next to the OH. This gives 1-phenylazo-2-naphthol, with an extended -N=N⁻ conjugated system that is orange-red.
    OptionReagentCoupling mediumDye formed
    (a)2-naphtholalkaline (NaOH)orange-red, 1-phenylazo-2-naphthol
    (b)1-naphtholalkalinecouples at C-4, not the standard orange-red dye
    (c)anilinemildly acidicyellow p-aminoazobenzene
    (d)1-naphthylaminemildly acidicamine coupling, not the NaOH reaction
  3. So. Reagent A is 2-naphthol, option (a). In NaOH it couples with benzenediazonium chloride to give the orange-red azo dye.

The idea to keep. Match the medium to the partner: phenols and naphthols couple in alkali (phenoxide), amines in mild acid. Phenol gives orange, 2-naphthol orange-red, aniline yellow.

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.