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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc217

Benzylamine, , is treated with / dil. at 273-278 K, and the mixture is then added to alkaline 2-naphthol. Which observation is correct?

  1. AA yellow oil of N-nitrosobenzylamine separates
  2. BNitrogen gas is evolved and no azo dye is formed; benzyl alcohol is the main organic product
  3. CA stable benzyldiazonium chloride is obtained, which couples at position 1 of 2-naphthol
  4. DA red azo dye is formed, as with aniline

Answer: B

Benzylamine is an aliphatic-type (benzylic) primary amine, with NH2 on the side-chain carbon. Its diazonium salt is not stabilised by ring resonance and decomposes at once to N2 and the carbocation, giving benzyl alcohol. No diazonium ion remains for coupling. N-Nitroso compounds arise from secondary amines.
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