This is one of the questions on an organic past paper I'm going through (no answer schemes)
http://imgur.com/v1KuKg9The first Q was to draw the Sn1 mechanism to form F
The next Q:
(ii) With reference to the reactive intermediate drawn in your mechanism in
part (c)(i), explain why nitrile G is formed in preference to F.
Is this because the carbocation intermediate has 3 resonance forms where the positive charge is on the ortho and para positions, but the para is preferred for some reason? Maybe due to sterics?
(iii) Draw an arrow-pushing mechanism for the formation of 1,2-
dimethylbenzene H and explain why it is the major product in the reaction.
I really have no idea on this and I'm not sure what I should be looking up in my textbooks etc. so if someone could point me in the right direction I'd be grateful!