Electrophilic addition

Electrophilic addition to alkenes can produce stereoisomers

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When cyclohexene is treated with bromine in carbon tetrachloride, the racemic anti-1,2-dibromocyclohexane is obtained exclusively. The bromonium ion is opened with inversion in an SN2 reaction. As the bromine can attack from either side we get both stereoisomers and a racemic mixture.

H. Slebocka-Tilk, C. Y. Zheng and R. S. Brown, J. Am. Chem. Soc., 1993, 115, 1347–1352.