Cyclohexene reacts with Osmium Tetroxide () followed by . In a completely separate parallel experiment, cyclohexene is treated with a peroxycarboxylic acid () followed by aqueous acid hydrolysis (). T

Question

Cyclohexene reacts with Osmium Tetroxide ($OsO_4$) followed by $NaHSO_3$. In a completely separate parallel experiment, cyclohexene is treated with a peroxycarboxylic acid ($RCO_3H$) followed by aqueous acid hydrolysis ($H_3O^+$). The stereochemistry of the resulting diols are respectively:

Prashant Kotian · Accepted Answer

Correct answer: C. forms a cyclic osmate ester intermediate, ensuring the simultaneous delivery of both oxygens to the same face (Syn-dihydroxylation) to yield cis-1,2-cyclohexanediol. forms an epoxide, which is then opened by via a backside attack, resulting in Anti-addition to yield trans-1,2-cyclohexanediol.

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