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

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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
Transcribed Image Text: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
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,
HO
HOCI
+
CH
O.
Na+
sodium hypochlorite
аcetic acid
OH
HOCI
+
H2O +
HC1
+
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
attacks the chlorine of the hypochlorite, which has a formal charge of +1.
охygen
Figure 8.2 Mechanism for Oxidation
H3C
H
-OH
CH 3
H2O
H
+ H20 + CF
Physical Constants
Compound
Mol. Wt (g/mol)
b.p. (°C)
Density
(g/mL)
0.96
m.p. (°C)
Cyclohexanol
Cyclohexanone
Dichloromethane
100.16
161.5
25.5
98.15
84.93
0.947
155
-47
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, HO HOCI + CH O. Na+ sodium hypochlorite аcetic acid OH HOCI + H2O + HC1 + 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 attacks the chlorine of the hypochlorite, which has a formal charge of +1. охygen Figure 8.2 Mechanism for Oxidation H3C H -OH CH 3 H2O H + H20 + CF Physical Constants Compound Mol. Wt (g/mol) b.p. (°C) Density (g/mL) 0.96 m.p. (°C) Cyclohexanol Cyclohexanone Dichloromethane 100.16 161.5 25.5 98.15 84.93 0.947 155 -47 1.325 39-40 -97
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