Problem: Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would be a) a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial.  b) a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial.  c) a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial.  d) a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial. 

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Problem Details

Cyclohexene reacts with bromine to yield 1,2-dibromocyclohexane. Molecules of the product would be

a) a racemic form and, in their most stable conformation, they would have both bromine atoms equatorial. 

b) a racemic form and, in their most stable conformation, they would have one bromine atom equatorial and one axial. 

c) a meso compound and, in its most stable conformation, it would have both bromine atoms equatorial. 

d) a meso compound and, in its most stable conformation, it would have one bromine atom equatorial and one axial. 

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Based on our data, we think this problem is relevant for Professor Dixon's class at UMD.