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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc087

4-Nitroaniline is diazotised with / dil. at 273-278 K and the cold solution is added to alkaline 2-naphthol. The major product is

  1. A3-(4-nitrophenylazo)-2-naphthol
  2. B1-(4-aminophenylazo)-2-naphthol
  3. C1-(4-nitrophenylazo)-2-naphthol
  4. D1-(phenylazo)-2-naphthol

Answer: C

Diazotisation converts the amino group only; the nitro group stays, giving 4-nitrobenzenediazonium chloride. This coupling partner attacks 2-naphthoxide at C-1, giving 1-(4-nitrophenylazo)-2-naphthol. No reducing agent is present, so the nitro group is not changed to amino.
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