Procedure: Set-up your 250 mL 2-necked round bottom flask as shown in Figure 8.3. Attach the thermometer using the red neoprene adapter. Add 6.0 mL cyclohexanol to the round bottom flask. In the 400 mL beaker, get 85 mL of bleach and add 4.0 mL glacial acetic acid in the hood. Pour the bleach and acetic acid mixture into your separatory funnel and suspend it by an iron ring as shown in Figure 8.3. If you have a separatory funnel that is furnished with a ground glass joint at the bottom, DO NOT connect the joints since you want to have a system that is open to the atmosphere. Figure 8.3 Separatory funnel iron ring thermometer ground glass thermometer adaptor plus rubber adaptor 250 mL round bottom flask Begin adding the bleach solution slowly a few drops at a time. Monitor the temperature. You want to maintain the temperature between 40 – 50 °C. Do not allow the temperature to rise above 50 °C. Use the cooling bath if necessary. And, do NOT allow the temperature to fall below 40 °C. Otherwise the oxidation will not go to completion. The addition should take about 15 – 20 minutes to complete. Be patient. Add a few mL of the bleach, swirl the flask to mix and monitor the temperature. When all of the bleach has been added, there should be a slight yellow color. If not, add more bleach until a faint yellow color persists. Sometimes it can be difficult to determine if there is actually a yellowish tint persists. Do not add more than 5-10 ml additional bleach. Holding a white piece of paper behind the flask can be helpful. After all the bleach has been added, allow the reaction mixture to stand for 15 minutes with occasional swirling. After 15 minutes, check the color of your reaction. If there is a slight yellow color, this indicates that there is an excess of hypochlorous acid. Add sodium bisulfite (NaHSO,) solution until the yellow color disappears. Sodium bisulfite is a mild reducing agent and it will react with the hypochlorous acid. A few mL is usually sufficient. Remove the separatory funnel and set-up your apparatus for a simple distillation as shown in Figure 8.4. Use the same 250-mL round bottom flask and use a 100 mL receiving flask. Transfer your thermometer to the