Vicinal halo alcohols (halohydrins) can be synthesized by treating epoxides with HX. (a)

Chapter 11, Problem 11.48

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Vicinal halo alcohols (halohydrins) can be synthesized by treating epoxides with HX. (a) Show how you would use this method to synthesize 2-chlorocyclopentanol from cyclopentene. (b) Would you expect the product to be cis-2-chlorocyclopentanol or trans-2- chlorocyclopentanol; that is, would you expect a net syn addition or a net anti addition of iCl and iOH? Explain.

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