ORGO lab 2

ORGO lab 2 - Dongkyu Kim Monday 2:00 Lab Instructor: Yu...

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Dongkyu Kim Monday 2:00 Lab Instructor: Yu Wang Dihydroxylation of Cyclohexene Abstract We constructed cyclohexane-1,2 diol by dihydroxylation of cyclohexene by reacting it with dimethyldioxirane (a product of oxone and acetone reaction). Through TLC analysis, it was determined that our product was cyclohexane-1,2- trans diol. R f for 4 (oxone) = 1.71cm/ 4.50cm = .380 Retention factor (R f ) of our oxone solution was close to R f of trans-diol. Introduction The main goal of this experiment was to synthesize cyclohexane-1,2 diol and determine whether it was in the cis or trans conformation. There are several ways of forming cyclohexane-1,2 diol from cyclohexene. One method is to react cyclohexene with KMnO 4 produces a cis-diol. Another way involves a reaction with I 2 and H 2 O produces a trans-diol. In this experiment, we utilize oxone to produce. Oxone produces dimethyldioxirane and reacts with cyclohexene when reacted with acetone. However, it is not known to us whether this produces a cis-diol or a trans- diol. TLC is a very useful technique that enables separation of compounds through adsorption. A silica gel in organic solvent allows for the solvent to move up and separate compounds according to their polarities. So two same compounds will travel the same distance up the plate. As a result, they have the same retention factors (see calculations). Therefore, TLC is an optimal method to determine an unknown compound. Main Reaction Oxone Dimethyldioxirane cis or trans formed in situ cyclohexane- 1,2 diol
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Table of Reagents: Compound Reagant Product MW (g/mol) Theoretical weight or volume Actual weight and/or volumes Moles (reagants)
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ORGO lab 2 - Dongkyu Kim Monday 2:00 Lab Instructor: Yu...

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