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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc262

The compound shown has two different nitrogen atoms. Select all the correct statements.

  1. AIt gives a diazonium salt on treatment with cold / at the primary aromatic amino group
  2. BIt gives a positive carbylamine test
  3. CWith benzenesulfonyl chloride the NH2 group forms a sulfonamide that dissolves in alkali
  4. DThe nitrogen is converted into an N-nitroso group by nitrous acid

Answer: A, B, C

The compound shown is N,N-dimethyl-p-phenylenediamine. The free aromatic NH2 behaves as a primary arylamine: diazotisation, carbylamine reaction and Hinsberg sulfonamide with acidic N-H (alkali soluble). The tertiary NMe2 nitrogen has no N-H and cannot form an N-nitroso compound.
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