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Which optical isomer of Styrene Oxide enter image description here would be produced if it is synthesized via epoxidation of the halohydrin. i.e.

enter image description here

Is there a way to deduce this? I assume it would depend on which isomer the halohydrin itself is since that too seems to have an assymetric Carbon atom?

Well, the halohydrin itself is produced from styrene which is optically inactive by the action of hypochlorous acid. Does this enable us to deduce theoritically the optical rotation of the final product i.e. Styrene Oxide?

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  • $\begingroup$ Thanks! Would there be a practical way to separate the optical isomers at scale for a tentative production process? Or would one rather choose an entirely different synthesis route;a route that starts from an optically pure reagent and utilizes chirality preserving reactions? $\endgroup$ – curious_cat Mar 3 '16 at 5:39
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Styrene and HClO are going to make a racemic mixture, in which case the epoxide will also be racemic, i.e. there should be no optical rotation.

An alternative would be to use the Jacobsen epoxidation, the Shi epoxidation or some other enantioselective epoxidation.

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