Problem 9.12: "Explain the stereochemistry of the addition of bromine to cis-2-butene." The margin note read: "Sir tricked us with this in 2002. The answer is meso compound, but the mechanism is anti addition. See diagram below."
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Modern Organic Chemistry : M.K. Jain, S.C. Sharma - Amazon.in Problem 9
: Principles of chirality, optical activity, and conformational analysis. Reactions : Aliphatic nucleophilic substitution ( ), addition to bonds, and elimination reactions. addition to bonds