[synthesis87]

from a cyclohexane.


What I tried doing was:

cyclohexane ---(radical bromination)----> bromocyclohexane ---(dehydrobromination)---> cyclohexene ---(bromination)---> 1,2-dibromocyclohexane ---(NaH, 2 propanol in diethyl ether)---> cyclohexadiene.


When I asked my professor, he wasn't so happy with the method. He said this was possible, but not the best way to form a cyclohexadiene... and I understand why, but I don't know what alternate method there could be 


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also, if I have, for instance: HO-CH₂-CH₂-Br
and I am trying to add H-CN by Sn2, what solvent should I put this in?

I'm not sure if I understand the whole solvent thing in general... for instance, when would you generally want a basic solution? aprotic? acidic?

Thanks!

[FeLiXe]

Why not add both bromines at the same time and eliminate at the same time. It's hard just to get the dibromo product. But the monobromo product is just as difficult to get und you'd have to do it twice. It's kind of the same idea as in that other elimination question.