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JEE Advanced levelOne or more correct optionsDifficulty 3 of 3nc088

Benzenediazonium chloride couples with each of the following under suitable conditions. Select the pairs in which the stated major product is correct.

  1. A4-methylphenol, alkaline: azo group para to
  2. B2-naphthol, alkaline: 1-(phenylazo)-2-naphthol
  3. Cphenol, alkaline: 4-hydroxyazobenzene
  4. DN,N-dimethylaniline, pH 4-5: azo group ortho to as the major product

Answer: B, C

Phenoxide couples para, giving 4-hydroxyazobenzene, and 2-naphthoxide couples at C-1. In 4-methylphenol the para position is occupied by , so the azo group goes ortho to . In N,N-dimethylaniline the free para position is preferred over the hindered ortho position.
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