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Posted 3 months ago

d) Predict the structures of the product(s) and provide a mechanism for the following reaction. Use the solid/dash wedge convention to show three dimensions. Explain the stereochemical outcome.
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Answer from Sia
Posted 3 months ago
Identify the reaction: The reaction described is an osmium tetroxide-catalyzed dihydroxylation of cyclohexene
Predict the product structure: The product of this reaction will be a cis-diol, with two hydroxyl groups added to the former double bond of cyclohexene. The stereochemistry will be cis due to the syn addition of the osmium tetroxide reagent
Provide a mechanism: The mechanism involves the formation of a cyclic osmate ester intermediate, followed by a reductive workup that cleaves the osmium-oxygen bonds and replaces them with hydrogen-oxygen bonds
Explain the stereochemical outcome: The addition of the hydroxyl groups occurs on the same side of the double bond (syn addition), resulting in a cis-diol. This is because the osmium tetroxide adds to the alkene in a concerted manner, forming a cyclic intermediate that preserves the relative positions of the substituents
The product is a cis-diol derived from cyclohexene, with both hydroxyl groups on the same side of the former double bond. The mechanism involves the formation of a cyclic osmate ester intermediate with syn addition of hydroxyl groups.
Key Concept
Dihydroxylation of alkenes with OsO4
OsO4 adds to alkenes like cyclohexene to form a cyclic osmate ester, which upon reductive workup yields a cis-diol with retention of stereochemistry due to syn addition.

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