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JEE Advanced levelSingle correct optionDifficulty 3 of 3nc216

Toluene is nitrated and the para isomer is isolated; this is reduced with , diazotised with / dil. at 273-278 K and coupled with phenol in alkaline medium. The final azo compound is

  1. A4-[(4-methylphenyl)diazenyl]phenol
  2. B4-[(4-nitrophenyl)diazenyl]phenol
  3. C4-[(3-methylphenyl)diazenyl]phenol
  4. D2-[(4-methylphenyl)diazenyl]phenol

Answer: A

4-Nitrotoluene is reduced to 4-methylaniline (p-toluidine), which gives 4-methylbenzenediazonium chloride. The para position of phenoxide is free, so coupling occurs there and the product is 4-[(4-methylphenyl)diazenyl]phenol.
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