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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Erikperik on September 25, 2015, 12:29:12 PM

Title: Additions to conjugated system
Post by: Erikperik on September 25, 2015, 12:29:12 PM

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.

Title: Re: Additions to conjugated system
Post by: orgopete on September 25, 2015, 02:48:04 PM

Hint, the intermediate is resonance stabilized.

Title: Re: Additions to conjugated system
Post by: Erikperik on September 25, 2015, 04:18:53 PM

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