Experiment 4 Handout


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DIHYDROXYLATION OF CYCLOHEXENE OBJECTIVES This experiment introduces you to the synthesis of the diol using new laboratory skills. Using Thin-Layer Chromatog- raphy you will determine weather the product is a cis or a trans diol. BACKGROUND Certain This experiment is not in your laboratory textbook so you will be required to use this handout to prepare your lab notebook with the procedures, chemicals and tasks that you will need to complete the lab. The theory for this experiment can be found in several sections in your text (as well as this handout) and are outlined below. You will need to read/review this background material in order to respond to the questions on the pre-lab quiz. Please read: Section 6.1 Introduction to Chromatography and 7.2 Thin Layer Chromatography (pages 179-184) Section 7.1 Introduction to Stereoisomers (pages 213-215) Section 7.2 Separation of Diastereomeric 1,2- Cyclohexanediols (pages 216-217) ADDITIONAL BACKGROUND. There are many ways to form cyclohex- ane-1,2 diol from cyclohexene. You can use KMnO 4 to form a cis-diol or iodine (I 2 ) and water to make a trans-diol, however a better way to make the diol is to use oxone. Oxone is a persulfate mix that reacts with acetone to produce dimethyldioxirane (Scheme 1). Dimethyldioxirane will react with cyclohexene to form cyclohexane-1,2-diol. Because we are working in microscale we’re not going to collect the product (cyclohexane 1,2 diol). We will spot the reaction mixture on a TLC plate along with authentic samples of cis and trans 1,2 diol. This will allow us to determine whether we formed a cis or trans diol in this oxone experiment. Scheme 1.
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