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Q.

(Z)-2-Butene reacts with Br2/H2O. The resulting bromohydrin when treated with methoxide in methanol undergoes an intramolecular SN2 reaction. Taking into consideration the stereochemical consequences of the reaction mechanism involved, choose the final product(s) of these transformations.

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a

(I) only

b

(II) only

c

(III) only

d

Equal amounts of (I) and (II)

answer is D.

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Detailed Solution

Bromohydrin Formation and Intramolecular SN2 Reaction

When (Z)-2-butene reacts with Br2/H2O, it forms bromohydrins with anti stereochemistry, where the bromine and hydroxyl groups add across the double bond in a trans manner.

These bromohydrins, upon treatment with sodium methoxide (NaOMe) in methanol, undergo an intramolecular SN2 reaction. The hydroxyl group attacks the adjacent carbon bearing bromine, displacing it via backside attack, leading to inversion of configuration at that carbon.

As a result, two enantiomeric epoxides are formed, specifically (2R,3R)-2,3-epoxybutane and (2S,3S)-2,3-epoxybutane.

This mechanism explains how stereochemical details of the reaction influence the final products, resulting from anti addition followed by intramolecular nucleophilic substitution with inversion. 

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