Question

Draw the major organic product formed when the compound shown below undergoes a reaction with HNO3 and H2SO4.

OAc

Answer 1

To solve this you need to recognize that the OAc branching off from the benzene ring is acetate. Being that the O is directly bonded to the benzene ring, it has lone pairs that it can donate, hence making it an electron donating group (activating group). Activating groups are ortho/para directors. In this reaction, we are undergoing nitration but at the para position from the acetate. Because of the size of the acetate and the NO2 group, you cannot put them ortho to one another due to repulsion. Therefore, draw both groups para to one another. The O in the OAc is part of the acetate already. You just have to draw the rest of it.

Answer 2

OAc is an ortho/para director OAc OAc NO2 O2N