Br2 will also react with alkenes to do electrophilic addition reactions. This is a non-radical reaction that has an interesting stereochemical outcome. Treatment of the optically-active methylcyclohexane shown below with bromine gives the product where Br2 has been added across the double bond.
a. Draw all possible stereoisomers that might be obtained. Use the “flat-ring” wedge/dash convention. Be sure that the methyl group is on the topmost carbon in all your structures. Each structure will be in a separate box with a roman numeral designator.
b. For EACH chiral carbon, label its stereochemistry as R or S.
c. Which structures are diasteromers? Use the roman numeral designators for this answer. If there are no diastereomers, write NONE.
d. Which structures are meso? Use the roman numeral designators for this answer. If there are no meso structures, write NONE.