[MarxG]

Hello everyone,

I am trying to do a synthesis problem, but for the life of me I cannot figure it out and was hoping someone could shed some light on it. I have attached the reaction to hopefully make it easier.

[Dan]

Please demonstrate that you have attempted the question. This is a Forum Rule.

[zsinger]

Try Radical Bromination first bubba!  Thats your hint.  I see the synthesis……not that difficult, but you must think!

[orgopete]

Try Radical Bromination first bubba!  Thats your hint.  I see the synthesis……not that difficult, but you must think!

Syntheses can have many paths. This is one, but not the one I would choose. I think the key step is anticipated to be a KOtBu elimination of a chloride. I'd start with a reaction with HCl. (By the way, I don't think the in the lab result will be as good as that anticipated by textbooks, but that is a different issue.)

[MarxG]

I apologize I didn't mean to not show work, I just found it difficult/awk. to put my scratch work into words.

Taking your hints I still get stuck..If I use HCl then I will break the double bond and I will have the chloride attached, I could eliminate this and then use oxymecuration to get an OH and methyl both at the top, but then I don't know how to remove the methyl group.

And in terms of free radical bromination I run into the same wall.

I hope that makes sense as I may be trying to approach this problem the completely wrong way.

[zsinger]

Yea, Orgopete's way is better.  Although these reactions NEVER come out cleanly in the lab.  I hate aromatic chemistry.  Never works just right!

[orgopete]

Hint, in either case, the intermediate is a secondary carbocation adjacent to a tertiary center.