Question

What products may form if the EAS reaction of acetanilide to form p-nitroacetanilide is not performed correctly?

A) 2,3,4,5,6-pentanitroacetanilide

B) 2,4-dinitroacetanilide

C) 2,4,6-trinitroacetanilide

D) 3,4-dinitroacetanilide

E) Both 2,4-dinitroacetanilide and 2,4,6-trinitroacetanilide are possible

Answer 1

I think the answer would be E.

As acetamido group (-NHCOCH3) in acetanilide is ortho and para directing and thus nitration of acetanilide produces p-nitroacetanilide and o-nitroacetanilide. Due to bulky acetamido group, the ortho position faces steric hindrance and thus p-nitroacetanilide is the major product. If the reaction is not performed correctly there is a possibility of substitution at 2,4 and 6 position only. Thus, 2,4-dinitro and 2,4,6-trinitro acetnilide are possible.

The position 3 and 4 are not activated by the acetamido group and thus substitution at these positions are not possible.