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When benzenediazonium chloride is treated with p -cresol in an alkaline medium, the major product formed is:

Options

  1. A5-hydroxy-2-methylazobenzene
  2. B2-hydroxy-5-methylazobenzene
  3. C4-hydroxyazobenzene
  4. Dp -tolyl phenyldiazenyl ether

Correct answer

B. 2-hydroxy-5-methylazobenzene

Step-by-step solution

Azo coupling is an electrophilic aromatic substitution where the diazonium ion acts as a weak electrophile. It requires a highly activated aromatic ring to react. In p -cresol (4-methylphenol), there are two substituents on the benzene ring: an - OH group and a - CH ₃ group. Both are activating and ortho/para directing, but the - OH group is a much stronger activating group than the - CH ₃ group. Therefore, the - OH group dictates the regiochemistry of the incoming electrophile. The position para to the - OH group

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