JEE MainChemistryAmines
p -Nitrotoluene is treated with Sn/HCl to give product A. Compound A is then reacted with NaNO ₂ and HCl at 273-278 K , followed by reaction with phenol in an alkaline medium to yield a major product B. The major products A and B are respectively:
Options
- AA = p -toluidine, B = 2-( p -tolylazo)phenol
- BA = m -toluidine, B = 4-( m -tolylazo)phenol
- CA = p -toluidine, B = 4-hydroxyazobenzene
- DA = p -toluidine, B = 4-( p -tolylazo)phenol
Correct answer
D. A = p -toluidine, B = 4-( p -tolylazo)phenol
Step-by-step solution
Reduction of p -nitrotoluene with Sn/HCl reduces the - NO ₂ group to an - NH ₂ group, yielding p -toluidine (Product A). Reaction of p -toluidine with NaNO ₂ and HCl at 273-278 K produces p -toluenediazonium chloride. This diazonium salt undergoes an electrophilic substitution (azo coupling) with phenol in an alkaline medium. The coupling preferentially occurs at the sterically less hindered para position of the phenol ring, yielding 4-( p -tolylazo)phenol (Product B) as the major product. Answer: A = p -toluidine,