Experiment #: 6
Title: Green Oxidation – Synthesis of Cyclohexanone from Cyclohexanol
Purpose:
is to synthesize cyclohexanone through the green oxidation of cyclohexanol using sodium
hypochlorite (common household bleach) as an environmentally friendly oxidizing agent. The
goal is to confirm the successful oxidation of a secondary alcohol to a ketone and to assess the
purity and identity of the product through chemical and instrumental analysis
Procedure:
1. Setup and Preparation:
a. Begin by assembling the reaction apparatus, which includes a 250 mL round-
bottom flask fitted with a magnetic stir bar, a thermometer, an addition
funnel, and a reflux condenser.
i. Ensure all glassware is clean and dry before use.
2. Addition of Reactants:
a. Measure 16.00 mL of cyclohexanol using a graduated cylinder.
i. Carefully transfer the cyclohexanol to the round-bottom flask.
b. Measure 7.00 mL of glacial acetic acid and use it to rinse any
residual cyclohexanol from the graduated cylinder into the flask.
i. Begin stirring the reaction mixture gently using a magnetic stirrer.
3. Preparation of Oxidizing Agent:
a. Measure 100.0 mL of household bleach (approximately 5–6%
sodium hypochlorite) and pour it into the addition funnel.
i. Check that the stopcock on the addition funnel is closed before filling
to prevent spillage.
4. Oxidation Reaction:
a. Slowly open the stopcock and add approximately 25 mL of bleach to the
reaction mixture to initiate the oxidation process.
b. Maintain a reaction temperature of approximately 45°C throughout the
procedure using an external water bath or ice bath as needed.
i. Gradually add the remaining 75 mL of bleach dropwise over the course
of 15 minutes, monitoring the temperature closely.
5. Second Bleach Addition:
a. After the initial addition, measure and add a second 100 mL portion of bleach
into the addition funnel.
i. Add this second portion dropwise over another 15-minute interval
while maintaining the reaction temperature near 45°C.
6. Post-Reaction Testing and pH Adjustment:
a. Use potassium iodide-starch paper to test for the presence of excess
hypochlorite; no blue color indicates complete reaction.
i. Test the pH using universal indicator paper. If the mixture is not slightly
basic, carefully add a small amount of sodium hydroxide solution until
the pH reaches slightly above neutral.
7. Distillation:
a. Set up for fractional distillation to separate and collect the cyclohexanone product.
Title: Green Oxidation – Synthesis of Cyclohexanone from Cyclohexanol
Purpose:
is to synthesize cyclohexanone through the green oxidation of cyclohexanol using sodium
hypochlorite (common household bleach) as an environmentally friendly oxidizing agent. The
goal is to confirm the successful oxidation of a secondary alcohol to a ketone and to assess the
purity and identity of the product through chemical and instrumental analysis
Procedure:
1. Setup and Preparation:
a. Begin by assembling the reaction apparatus, which includes a 250 mL round-
bottom flask fitted with a magnetic stir bar, a thermometer, an addition
funnel, and a reflux condenser.
i. Ensure all glassware is clean and dry before use.
2. Addition of Reactants:
a. Measure 16.00 mL of cyclohexanol using a graduated cylinder.
i. Carefully transfer the cyclohexanol to the round-bottom flask.
b. Measure 7.00 mL of glacial acetic acid and use it to rinse any
residual cyclohexanol from the graduated cylinder into the flask.
i. Begin stirring the reaction mixture gently using a magnetic stirrer.
3. Preparation of Oxidizing Agent:
a. Measure 100.0 mL of household bleach (approximately 5–6%
sodium hypochlorite) and pour it into the addition funnel.
i. Check that the stopcock on the addition funnel is closed before filling
to prevent spillage.
4. Oxidation Reaction:
a. Slowly open the stopcock and add approximately 25 mL of bleach to the
reaction mixture to initiate the oxidation process.
b. Maintain a reaction temperature of approximately 45°C throughout the
procedure using an external water bath or ice bath as needed.
i. Gradually add the remaining 75 mL of bleach dropwise over the course
of 15 minutes, monitoring the temperature closely.
5. Second Bleach Addition:
a. After the initial addition, measure and add a second 100 mL portion of bleach
into the addition funnel.
i. Add this second portion dropwise over another 15-minute interval
while maintaining the reaction temperature near 45°C.
6. Post-Reaction Testing and pH Adjustment:
a. Use potassium iodide-starch paper to test for the presence of excess
hypochlorite; no blue color indicates complete reaction.
i. Test the pH using universal indicator paper. If the mixture is not slightly
basic, carefully add a small amount of sodium hydroxide solution until
the pH reaches slightly above neutral.
7. Distillation:
a. Set up for fractional distillation to separate and collect the cyclohexanone product.
