What best decribes the product(s) obtained when cis-3-hexene is treated with Br2 and H2O, followed by NaOH?Select answer from the options belowan enantiomerically pure epoxidean enantiomerically pure diola meso diola 1:1 mixture of enantiomeric diolsa meso epoxidea 1:1 mixture of enantiomeric epoxides
Question
What best decribes the product(s) obtained when cis-3-hexene is treated with Br2 and H2O, followed by NaOH?Select answer from the options belowan enantiomerically pure epoxidean enantiomerically pure diola meso diola 1:1 mixture of enantiomeric diolsa meso epoxidea 1:1 mixture of enantiomeric epoxides
Solution
The reaction of cis-3-hexene with Br2 and H2O is a halohydrin formation reaction. This reaction will result in the formation of a bromohydrin, where the bromine and the OH group are added across the double bond.
In the next step, when the bromohydrin is treated with NaOH, it undergoes intramolecular substitution reaction (SN2) to form an epoxide.
However, the initial bromohydrin formation is not stereospecific, meaning it can form two enantiomers. Therefore, the final product will be a 1:1 mixture of enantiomeric epoxides.
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