Orgo Lab 7 - Dihydroxylation of 1,2-cyclohexene and TLC...

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Dihydroxylation of 1,2-cyclohexene and TLC Abstract: The main purpose of this experiment was to take the reactant 1,2-cyclohexene and convert it into 1,2-cyclohexanediol using two different methods. The first method used dimethydioxirane, while the second method used potassium permanganate (KMnO 4 ). The use of two different methods created two different forms of 1,2-cyclohexanediol. One of which was cis-1,2-cyclohexanediol while the other was trans-1,2-cyclohexanediol. However, because cis and trans molecules have nearly identical properties it was difficult to tell which product was which. The way to determine this was to use TLC or Thin Layer Chromatography. The results from the TLC showed that the reaction using dimethyldioxirane created trans-1,2-cyclohexanediol, while the method that used KMnO 4 created cis-1,2-cyclohexanediol. The general reactions are shown below: Introduction: This experiment involved the mixing of certain reactants in order to create two different forms of 1,2-cyclohexanediol: cis and trans. The first reaction involved a reaction between dimethyldioxirane and cyclohexene in order to form one of the diastereomers, and the second reaction involved a reaction between KMnO4 and cyclohexane in order to form the other diastereomer of 1,2-cyclohexanediol. Diastereomers are similar to enantiomers, however they are not mirror images of each other. In other words, they are configural isomers that are not enantiomers. Molecules that are diastereomers of each other have different properties from each other such as different chemical and physical properties. Therefore, the cis-1,2-cyclohexanediol and trans-1,2-cyclohexanediol that were formed in this experiment had different properties from each other. This fact was taken advantage of in order to determine which reaction created which product, because this was not known at the beginning of the experiment. In order to determine which product was cis and which was trans a Thin Layer Chromatography was performed. Thin Layer Chromatography is an experimental tool that separates substances based on the affinities that they have for either the mobile phase or

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