Consider the electrophilic aromatic nitration of p -methylacetanilide ( N -(4-methylphenyl)acetamide). Identify the position of the incoming nitro group in the major product relative to the existing groups on the benzene ring.

Step-by-step solution

In p -methylacetanilide, the benzene ring has two substituents: an acetamido group ( - NHCOCH ₃ ) and a methyl group ( - CH ₃ ) situated para to each other. Both groups are ortho/para directing. However, the - NHCOCH ₃ group is a moderately strong activating group due to the lone pair on nitrogen, whereas the - CH ₃ group is weakly activating via hyperconjugation. When multiple directing groups are present, the more powerfully activating group dictates the position of the incoming electrophile. Thus, the - NHCOCH ₃