[Erikperik]

Hi
So this problem got me stumped: Which two products do you get when you add 1 mole HBr to 1 mole 1,4-dimethyl-1,3-cyclohexadiene?

I thought the answer was 4-bromo-1,4-dimethylcyclohexene and 3-bromo-3,6-dimethylcyclohexene.

But I'm told the answer is 3-bromo-3,6-dimethylcyclohexene and 3-bromo-1,4-dimethylcyclohexene.

[orgopete]

Hint, the intermediate is resonance stabilized.

[Erikperik]

Cheers mate. It helped. Took a little while, but I figured it out.