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Chapter 8: Q. 8-8-71E (page 262)

Hydroxylation of cis-2-butene with OsO4yields a different product than hydroxylation of trans-2-butene. Draw the structure, show the stereochemistry of each product, and explain the difference between them.

Short Answer

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Hydroxylation of an alkene with osmium tetroxide happens with syn stereochemistry. Cis reactant leads to the formation of cis product.The reaction occurs by forming a cyclic osmate intermediate in a single step reaction with an alkene, which on oxidation leads to 1,2 diol.

Oxidation of osmate does not affect the stereochemistry of the carbon-oxygen bond.

Step by step solution

01

Hydroxylation of cis-2-butene with OsO4

Hydroxylation of an alkene with osmium tetroxide happens with syn stereochemistry. Cis reactant leads to the formation of cis product.The reaction occurs by forming a cyclic osmate intermediate in a single step reaction with an alkene, which on oxidation leads to 1,2 diol.

Oxidation of osmate does not affect the stereochemistry of the carbon-oxygen bond.

02

Hydroxylation of Trans-2-butene with OsO4

Hydroxylation of an alkene with osmium tetroxide happens with syn stereochemistry. Cis reactant leads to the formation of cis product. The reaction occurs with the formation of a cyclic osmate intermediate in a single step reaction with an alkene, which on oxidation leads to the formation of 1,2 diol.

Oxidation of osmate does not affect the stereochemistry of the carbon-oxygen bond.

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