Boiling point: Trans vs. Cis 1,2-dibromocyclohexane

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nfg05

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So one of the solutions in my review materials said that trans-1,2-dibromocyclohexane has a lower vapor pressure (and thus stronger intermolecular attractions and a higher bp) compared to cis-1,2-dibromocyclohexane. I'm probably not taking something more important into account, but to me cis should have the higher bp because the molecule is more polar overall (the two C-Br dipoles point in the same direction as opposed to working against each other in the trans molecule).

Anyone care to explain why the trans has a higher bp than the cis? Is it something about stacking better or something because I've never really understood how that impacts mp/bp. Even if this problem has nothing to do with "packing in better," I'd still like to hear about that and its impact on mp/bp :laugh:.
 
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