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JEE Advanced levelSingle correct optionDifficulty 3 of 3si258

The compound shown is used as the coupling partner in alkaline solution. Which of the structures shown, when treated with /HCl at 273-278 K and then added to the compound shown, gives a red azo dye?

  1. AStructure A
  2. BStructure B
  3. CStructure C
  4. DStructure D

Answer: C

An azo dye needs a diazonium salt, made only from a primary aromatic amine. C (p-toluidine) gives it. A (benzylamine) is an aliphatic amine whose diazonium decomposes at once, B is a secondary amine (gives an N-nitrosoamine) and D a tertiary aromatic amine (ring nitrosation).
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