Sciencemadness Discussion Board

1,2 dibromocyclohexane reaction in KI and acetone

Meltonium - 14-3-2018 at 14:57

Hey, y'all.

I've got this problem in my review packet for organic chemistry. It gives a reaction where (1R, 2R) dibromocyclohexane reacts with potassium iodide in acetone to yield cyclohexene.

So far in class, we have gone over the substitution and elimination mechanisms, and I understand them for the most part (my professor likes to teach us without teaching us if you know what I mean) but I have no idea where to begin with this one!

I tried searching for solutions online and the only thing that I dod find was the Finklestein Reactions where the Iodide replaces the bromines through an Sn2 mechanism, simple. But, I do not see how that would get me to a place where I could take away both bromines and end up with a singular alkene.

I mean I could probably figure something out I was allowed to choose the reagents, but all that is given is KI and acetone.

P.S. the question also asks to explain why (1R, 2S) dibromocyclohexane cannot form cyclohexene, but I'm pretty sure I know that's because of the hydrogen placements.