Dihydroxylation of cyclohexene

Dihydroxylation of cyclohexene - Daanish Chawala October 5...

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Daanish Chawala October 5, 2010 Dihydroxylation of cyclohexene Abstract: We synthesized cyclohexane-1,2 diol by dihydroxylation of cyclohexene by reacting it with dimethyldioxirane (a product of oxone and acetone reaction). Thin layer chromatography (TLC) revealed that the diol we obtained was the trans conformation. Introduction: The purpose of this experiment was to synthesize cyclohexane-1,2 diol and determine whether it was in the cis or trans conformation. There are several possible ways of forming cyclohexane-1,2 diol from cyclohexene. One way, which involves reacting coclohexene with KMnO 4 produces a cis-diol whereas another way involving a reaction with I 2 and water produces a trans-diol. Another possibility (the one that is utilized in this experiment) produces a diol using oxone, a persulfate mix that, when reacted with acetone, produces dimethyldioxirane which in turn reacts with cyclohexene. However, it is unknown to us whether this produces a cis-diol or a trans-diol. Thin layer chromatography is a technique that allows for separation of compounds via solid-liquid adsorption. A silica gel (polar molecule) coated plate placed in organic solvent allows for the solvent to travel up the plate and separate compounds spotted near the bottom of the plate based on their polarities. By this logic, two compounds that are exactly the same should be separated the same way and will travel the same distance up the plate—in other words, they have the same retention factors (see calculations). Clearly, then, TLC is an ideal way to determine an unknown compound so long as pure forms of all of the possibilities are available for use as controls. Table of Reagents:
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This note was uploaded on 01/27/2012 for the course CHEM CHEM-UA taught by Professor Jones during the Fall '11 term at NYU.

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Dihydroxylation of cyclohexene - Daanish Chawala October 5...

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