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JEE Main levelSingle correct optionDifficulty 2 of 3nc082

Benzenediazonium chloride is added to an alkaline solution of 4-methylphenol (p-cresol). The major product is

  1. A4-methyl-2-(phenylazo)phenol (azo group ortho to )
  2. B3-(phenylazo)-4-methylphenol (azo group meta to )
  3. Cno coupling, because the para position is blocked
  4. DO-coupled product

Answer: A

Phenoxide directs coupling to ortho/para positions. When the para position holds a methyl group, coupling takes place at the ortho position, giving 4-methyl-2-(phenylazo)phenol. Coupling does not occur meta to the oxygen, and the C-coupled azo compound is the product, not an azo ether.
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