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Leaving Group Conversions - Using HX
12. Alcohols, Ethers, Epoxides and Thiols / Leaving Group Conversions - Using HX / Problem 7

The reaction of an optically active trans-2-bromocyclohexanol with concentrated HBr solution results in optically inactive product trans-1,2-dibromocyclohexane (racemic). Show a mechanism showing how the reaction proceeds seemingly with complete retention of configuration, but actually with racemization. [Hint: Refer to the mechanism of the reaction when cyclohexene reacts with Br2 in water to form trans-2-bromocyclohexanol.] 

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