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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc274

The amine shown is treated with excess bromine water, the product is diazotised at 0-5 C, and the diazonium salt is treated with . Which structure is the final organic product?

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

Answer: C

The compound shown is aniline. Excess bromine water brominates all three activated positions (2,4,6) to give 2,4,6-tribromoaniline. Diazotisation and deamination with hypophosphorous acid replace the amino group by hydrogen, leaving the bromines in place: 1,3,5-tribromobenzene.
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