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08 & 7 8 CO + U as you did in Experiment 9 and as shown in the "How to Tabulate Spectral Data" handout on Canvas). Don't forget to label the spectrum and provide a labeled structure next to your data table! POST-LAB QUESTIONS: 1. Draw a complete mechanism for your assigned reaction. 2. Calculate the expected 'H NMR chemical shift values for your alkene (show and label all work for full credit). Discuss and compare to your actual values. Explain how your spectrum is consistent with your product. J к M

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Corinne Calculate the percent yield of your product, showing all Sofety Information Glacial acetic acid is a dehydrating agent, an irritant, and causes burns. Au contact with the skin, eyes, and clothing Dispense in a hood, Sodium hypochlorite solutions can emit Chorine gas, which is a respiratory and eye irritant. Dispense it in a fume hood, Suggested Waste Disposal Aqueous solutions may be washed down the drain with plenty of water. The dichloromethane recovered by distillation should be placed in the appropriately labeled bottle in the hood. You will be tuming your product in to the instructor PROCEDURE (Be sure to note your observations in your notebook as you work.) Z-ethyl-1,3-hexanediol Setting up the reaction: Welch 2.0 g of 2-ethyl-1,3-hexanediol a viscous liquid) in a 50-ml Erlenmeyer flask. Add 15 ml of glacial acetic acid and your magnetic stir bar to the Erlenmeyer and place it in an e-bath on the stirrer-hot plate. With stirring slowly add 16 ml of aqueous sodium hypochlorite solution (%, household bleach, density 1.084 g/mL) dropwise while monitoring the temperature. Do not allow the temperature to rise above 30 °C II. 2,2,4-trimethyl-1,3-pentanediol Setting up the reaction: Weigh 20g of 2.2A-trimethyl-1,3 pentanediolina Som Erlenmeyer flask, smashing any lumps. Add 15 ml of glacial acetic acid and your magnetic stir bar to the Erlenmeyer. Stir to be sure it is all dissolved and place it in an ice-bath on the stirrer-hot plate. With stirring slowly add 16 mL of aqueous sodium hypochlorite solution (8%, household bleach, density 1.084 /m/ dropwise while monitoring the temperature. Do not allow the temperature to rise above 30 °C II. Both diols Completing the reaction: Stir the reaction solution at room temperature for a period of 1 hour To ensure the presence of excess hypochlorite during the reaction period, test the reaction mixture periodically for excess hypochlorite by transferring a drop of the reaction mixture to starch-lodine paper. If the paper does not turn dark blue/black/brown) within a few seconds, add enough bleach (about 0.5 ml at a time to the reaction mixture to give a positive test. The reaction should have a greenish yellow color while excess hypochlorite la present Working up the reaction and isolating the product Ful a 100 ml, beaker about half full of ice and add 10 ml of saturated sodium chloride solution (brine) to it. Pour your reaction mixture into the ice brine and stir well. Pour into your separatory funnel and extract the aqueous mature three times with 10- ml. portions of dichloromethane. Keep track of which layer is which during the extractions. Combine the three dichloromethane extracts, return them to the separatory funnel and extract them with two 10- ml portions of saturated sodium carbonate (be sure to vent, CO, gas will be produced). Then extract the dichloromethane solution with CHEM 220 Golden West College 110 مهم 1