Which site is more favorable for electrophilic aromatic substitution in O-Acetotoluidide?
The answer given in my textbook says the site para to acetamide group is more favorable, however I believe the site para to methyl group should be more favorable. Here are the reasons:
1) Because of sterric inhibition of resonance, acetamide group will be slightly out of plane thereby decreasing the quality of resonance.
2) Because of hyperconjugation by 3 alpha hydrogens, electron density will increase 3 times each at sites ortho and para to methyl group. This means that methyl group due to hyperconjugation will lead to nine resonance structures as opposed to just three in acetamide.
So, because of these two reasons, I think site ortho to methyl group should be more favorable(ortho will be less favorable because of sterric hindrance).
Am I missing something or the answer given in the book is wrong?