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Experiment 8 Preparation of Cyclohexanone by Hypochlorite Oxidation In this experiment we will prepare cyclohexanone from cyclohexanol using hypochlorite oxidation. We will use common household bleach that is a 5.25% (0.75 M) aqueous solution of sodium hypochlorite. The overall reaction is shown in Figure 8.1. Figure 8.1 Oxidation of Cyclohexanol Na* OCI CH; HOCI CH: Na* sodium hypochlorite acetic acid OH HOCI H2O HCI cyclohexanol cyclohexanone The exact reaction mechanism is not known but a plausible mechanism is given below. It is known that the mechanism does not involve free radicals and that yields are better in acidic rather than basic conditions. This is why we use acetic acid. It reacts with the sodium hypochlorite to give hypochlorous acid, which then reacts with the oxygen of the alcohol. Note the oxygen is more electronegative than chlorine so the oxygen attacks the chlorine of the hypochlorite, which has a formal charge of +1. Figure 82 Mechanism for Oxidation H;C H -OH H2O + H,0 + CF Physical Constants Compound Mol. Wt (g/mol) Density (g/mL) b.p. (°C) m.p. (°C) Cyclohexanol Cyclohexanone Dichloromethane 100.16 0.96 161.5 25.5 98.15 0.947 155 -47 84.93 1.325 39-40 -97

Experiment 8 Preparation of Cyclohexanone by Hypochlorite Oxidation In this experiment we will prepare cyclohexanone from cyclohexanol using hypochlorite oxidation. We will use common household bleach that is a 5.25% (0.75 M) aqueous solution of sodium hypochlorite. The overall reaction is shown in Figure 8.1. Figure 8.1 Oxidation of Cyclohexanol Na* OCI CH; HOCI CH: Na* sodium hypochlorite acetic acid OH HOCI H2O HCI cyclohexanol cyclohexanone The exact reaction mechanism is not known but a plausible mechanism is given below. It is known that the mechanism does not involve free radicals and that yields are better in acidic rather than basic conditions. This is why we use acetic acid. It reacts with the sodium hypochlorite to give hypochlorous acid, which then reacts with the oxygen of the alcohol. Note the oxygen is more electronegative than chlorine so the oxygen attacks the chlorine of the hypochlorite, which has a formal charge of +1. Figure 82 Mechanism for Oxidation H;C H -OH H2O + H,0 + CF Physical Constants Compound Mol. Wt (g/mol) Density (g/mL) b.p. (°C) m.p. (°C) Cyclohexanol Cyclohexanone Dichloromethane 100.16 0.96 161.5 25.5 98.15 0.947 155 -47 84.93 1.325 39-40 -97

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Experiment 8 Preparation of Cyclohexanone by Hypochlorite Oxidation In this experiment we will prepare cyclohexanone from cyclohexanol using hypochlorite oxidation. We will use common household bleach that is a 5.25% (0.75 M) aqueous solution of sodium hypochlorite. The overall reaction is shown in Figure 8.1. Figure 8.1 Oxidation of Cyclohexanol Na* OCI CH; HOCI CH: Na* sodium hypochlorite acetic acid OH HOCI H2O HCI cyclohexanol cyclohexanone The exact reaction mechanism is not known but a plausible mechanism is given below. It is known that the mechanism does not involve free radicals and that yields are better in acidic rather than basic conditions. This is why we use acetic acid. It reacts with the sodium hypochlorite to give hypochlorous acid, which then reacts with the oxygen of the alcohol. Note the oxygen is more electronegative than chlorine so the oxygen attacks the chlorine of the hypochlorite, which has a formal charge of +1. Figure 82 Mechanism for Oxidation H;C H -OH H2O + H,0 + CF Physical Constants Compound Mol. Wt (g/mol) Density (g/mL) b.p. (°C) m.p. (°C) Cyclohexanol Cyclohexanone Dichloromethane 100.16 0.96 161.5 25.5 98.15 0.947 155 -47 84.93 1.325 39-40 -97
Transcribed Image Text:Experiment 8 Preparation of Cyclohexanone by Hypochlorite Oxidation In this experiment we will prepare cyclohexanone from cyclohexanol using hypochlorite oxidation. We will use common household bleach that is a 5.25% (0.75 M) aqueous solution of sodium hypochlorite. The overall reaction is shown in Figure 8.1. Figure 8.1 Oxidation of Cyclohexanol Na* OCI CH; HOCI CH: Na* sodium hypochlorite acetic acid OH HOCI H2O HCI cyclohexanol cyclohexanone The exact reaction mechanism is not known but a plausible mechanism is given below. It is known that the mechanism does not involve free radicals and that yields are better in acidic rather than basic conditions. This is why we use acetic acid. It reacts with the sodium hypochlorite to give hypochlorous acid, which then reacts with the oxygen of the alcohol. Note the oxygen is more electronegative than chlorine so the oxygen attacks the chlorine of the hypochlorite, which has a formal charge of +1. Figure 82 Mechanism for Oxidation H;C H -OH H2O + H,0 + CF Physical Constants Compound Mol. Wt (g/mol) Density (g/mL) b.p. (°C) m.p. (°C) Cyclohexanol Cyclohexanone Dichloromethane 100.16 0.96 161.5 25.5 98.15 0.947 155 -47 84.93 1.325 39-40 -97
Figure 8.4 thermometer thermometer adaptor (ground glass adaptor plus rubber adaptor) blue plastic clamp water out water in blue plastic clamp 250 mL Round bottom flask ground glass stopper or small cork metal clamp boiling chips heating mantle 100 mL round bottom flask + Plug to Rheostat three-way adapter as shown in Figure 8.4. Place a secure cork in the small opening. Add a few boiling chips and distill your product, setting the rheostat on the heating mantle to about 70-80 V. This will be a steam distillation. You will distill a mixture of water and cyclohexanone. Continue the distillation until you have collected about 40 mL. You should see a layer of cyclohexanone on the top and an aqueous layer of water and acetic acid on the bottom. Work-up When you have collected 40 mL stop the distillation. Remove the receiving flask and CAREFULLY add solid sodium carbonate (Na,CO,) using your spatula until you have neutralized all of the acetic acid that distilled over with your product. Add a small spatula tip of the solid sodium carbonate and stir with your spatula. You should see evolution of CO, gas. DO NOT ADD THE SODIUM CARBONATE TOO QUICKLY TO THE SOLUTION BECAUSE IT CAN BUBBLE OVER. Keep adding the solid until there is no more bubbling. Remove some of the aqueous layer on the bottom with a medicine dropper and test with litmus to see that it is neutral. Cyclohexanone has some solubility in water. Add solid sodium chloride (add about 0.2 g of NaCl per milliliter of water present) to salt out the cyclohexanone from the water layer. Just as we did in the cyclohexene experiment, the idea is to saturate the aqueous layer with the very polar sodium chloride to drive the cyclohexanone from the water layer. Do not add too much of the sodium chloride. Add a spatula tip full, stir to dissolve and then add a bit more. Continue adding the NaCl until you see some solid material remaining.
Transcribed Image Text:Figure 8.4 thermometer thermometer adaptor (ground glass adaptor plus rubber adaptor) blue plastic clamp water out water in blue plastic clamp 250 mL Round bottom flask ground glass stopper or small cork metal clamp boiling chips heating mantle 100 mL round bottom flask + Plug to Rheostat three-way adapter as shown in Figure 8.4. Place a secure cork in the small opening. Add a few boiling chips and distill your product, setting the rheostat on the heating mantle to about 70-80 V. This will be a steam distillation. You will distill a mixture of water and cyclohexanone. Continue the distillation until you have collected about 40 mL. You should see a layer of cyclohexanone on the top and an aqueous layer of water and acetic acid on the bottom. Work-up When you have collected 40 mL stop the distillation. Remove the receiving flask and CAREFULLY add solid sodium carbonate (Na,CO,) using your spatula until you have neutralized all of the acetic acid that distilled over with your product. Add a small spatula tip of the solid sodium carbonate and stir with your spatula. You should see evolution of CO, gas. DO NOT ADD THE SODIUM CARBONATE TOO QUICKLY TO THE SOLUTION BECAUSE IT CAN BUBBLE OVER. Keep adding the solid until there is no more bubbling. Remove some of the aqueous layer on the bottom with a medicine dropper and test with litmus to see that it is neutral. Cyclohexanone has some solubility in water. Add solid sodium chloride (add about 0.2 g of NaCl per milliliter of water present) to salt out the cyclohexanone from the water layer. Just as we did in the cyclohexene experiment, the idea is to saturate the aqueous layer with the very polar sodium chloride to drive the cyclohexanone from the water layer. Do not add too much of the sodium chloride. Add a spatula tip full, stir to dissolve and then add a bit more. Continue adding the NaCl until you see some solid material remaining.
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