Redox Reactions and Volumetric AnalysishardNUMERICAL

How many distinct stereoisomers are possible for the final major organic product formed when cyclopeRedox Reactions and Volumetric Analysis Chemistry Question

Question

How many distinct stereoisomers are possible for the final major organic product formed when cyclopentene reacts with $OsO_4$ followed by $NaHSO_3$ aqueous workup?

Answer: 1

💡 Solution & Explanation

The reaction of a cyclic alkene with $OsO_4$ is a stereospecific syn-dihydroxylation. The product is exclusively cis-1,2-cyclopentanediol. Because this cis-isomer possesses an internal plane of symmetry, it is a meso compound. Therefore, there are no enantiomers, and only 1 distinct stereoisomer exists.

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