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JEE Main levelSingle correct optionDifficulty 2 of 3nc135

Benzenediazonium chloride reacts with N,N-dimethylaniline at pH 4-5. The major product is

  1. A4-(phenylazo)-N,N-dimethylaniline (p-dimethylaminoazobenzene)
  2. B2-(phenylazo)-N,N-dimethylaniline
  3. CN-nitroso-N-methylaniline
  4. DN,N-dimethyl-4-nitrosoaniline

Answer: A

The diazonium ion is a weak electrophile and attacks the strongly activated para position of N,N-dimethylaniline (mildly acidic medium), giving the yellow azo dye. Ortho attack is minor because of sterics. The nitroso compounds arise from nitrous acid, not from a diazonium salt.
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