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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc048

Compound A, , gives a positive carbylamine test. On treatment with at 273-278 K, then , then hydrolysis with aqueous acid, and finally vigorous oxidation with hot alkaline , it gives benzene-1,4-dicarboxylic acid (terephthalic acid). A is:

  1. AN-methylaniline
  2. B4-methylaniline
  3. Cbenzylamine,
  4. D3-methylaniline

Answer: B

The carbylamine test shows a primary amine. Diazotisation, and hydrolysis convert the amino group into a carboxylic acid group; oxidation of the remaining side chain methyl group to carboxyl gives terephthalic acid only if the two groups are para. So A is 4-methylaniline. Benzylamine, a primary aliphatic amine, would not give a diazonium salt, and N-methylaniline is secondary.
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