Fundamentals of Organic ChemistryChemistryAmines
Identify the major product C in the following reaction sequence:
Correct answer
1
Step-by-step solution
Reaction of p -toluidine with acetic anhydride in the presence of pyridine yields N -(4-methylphenyl)acetamide (compound A). This acetylation protects the - NH ₂ group and prevents polysubstitution. Compound A undergoes electrophilic aromatic substitution with Cl ₂ and AlCl ₃ . The - NHCOCH ₃ group is a stronger activating and ortho/para-directing group compared to the - CH ₃ group. Since the para position is blocked, the incoming chlorine electrophile is directed to the position ortho to the - NHCOCH ₃ group, form