4.StereochemistryofDihydroxylationlab - Stereochemistry of...

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Stereochemistry of Dihydroxylation Reactions Question: Can the stereochemical outcome of dihydroxylation reactions be determined by thin layer chromatography? Overview: In this experiment, you will perform two reactions that transform alkenes into diols. While similar in functional group transformation, these reactions may lead to stereochemically different products. The two possible products are diastereomers of one another, and therefore have different physical chracteristics. After performing the reactions, you will characterize the crude reaction mixtures to determine if you formed a mix of trans enantiomers, the cis product, or a mixture of cis and trans diols. (Figure 1) OH OH + OH OH OH OH ? ? Figure 1 In this experiment, you will use a common oxidizing agent, KMnO 4 . You will also use an oxidizer that you may not have discussed in lecture called Oxone ®. Oxone is a persulfate mix that reacts with acetone to produce dimethyldioxirane.
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Procedure : Oxone reaction Dissolve 0.40 g oxone ® in 2.0 mL of water by shaking vigorously in a sealed vial.
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This note was uploaded on 05/15/2011 for the course CHM 241 taught by Professor Jennifermorris during the Winter '09 term at Grand Valley State University.

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4.StereochemistryofDihydroxylationlab - Stereochemistry of...

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