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JEE Main levelSingle correct optionDifficulty 2 of 3nc078

Coupling of benzenediazonium chloride with N,N-dimethylaniline is carried out at pH 4-5 and not at pH 10 because at pH 10

  1. AN,N-dimethylaniline is converted into its anilinium ion
  2. Bthe dimethylamino group is hydrolysed by alkali
  3. Cnitrogen gas is evolved from the amine
  4. Dthe diazonium ion is largely converted into a non-electrophilic diazohydroxide / diazotate species

Answer: D

As pH rises, the diazonium ion adds hydroxide to give and then the diazotate ion, which is not electrophilic. At pH 4-5 the diazonium ion persists and the amine is still mostly unprotonated. At pH 10 the amine is not protonated, so that distractor is wrong.
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