JEE Advanced levelSingle correct optionDifficulty 3 of 3nc216
Toluene is nitrated and the para isomer is isolated; this is reduced with Sn/HCl, diazotised with NaNOX2 / dil. HCl at 273-278 K and coupled with phenol in alkaline medium. The final azo compound is
A4-[(4-methylphenyl)diazenyl]phenol
B4-[(4-nitrophenyl)diazenyl]phenol
C4-[(3-methylphenyl)diazenyl]phenol
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.