CHEM 202L
Name: ________________________________
Oxidation of Borneol
Ha
OH
NaOCl
H
CH3COOH
Borneol
O Cl
H
O
H
slow
O
Camphor
Procedure:
To a 50 ml round-bottom flask, add (0.360 g) of Borneol, (1.0 ml) acetone, and (0.30 ml) of
glacial acetic acid. Attach a water condenser and place the round-bottom flask into a water bath at
about 50C. (Use a 150 ml beaker for the water bath). It is important that the temperature of the
water bath remain at 50C during the entire period.
Addition of Sodium Hypochlorite:
Measure out (6 ml) of 6% hypochlorite solution in a 10 ml graduated cylinder. Use a Pasteur
pipette to drop wise add (0.5 ml) of the sodium hypochlorite solution every 4 minutes through the top
of the water condenser. The addition will take 48 minutes to complete. Continue to stir and heat the
mixture during the 48-minute period. After the addition, heat and stir the mixture for an additional 15
minutes.
Extraction of Camphor:
When the reaction time is complete, allow the mixture to cool to room temperature. Remove
the water condenser, transfer the mixture to a test tube and add (3 ml) of dichloromethane to extract
the camphor. Cap and shake well. Remove the organic layer and add another (3 ml) aliquot of
dichloromethane to the aqueous layer to remove any residual product. Shake, separate, and remove
the organic layer. Repeat one more time.
Combine all three dichloromethane layers in a test tube and wash with (3ml) of aqueous
saturated sodium bicarbonate solution. Stir till the bubbling ceases, cap and shake. Use a Pasteur
pipette to remove the upper aqueous layer. Wash the organic phase with (3 ml) aqueous sodium
bisulfate. Siphon off the top aqueous layer and perform a last wash with (3 ml) of water. Transfer the
organic layer to a beaker, taking care to rinse the test tube with a small volume of dichloromethane. Dry
the “goodies” with anhydrous sodium sulfate. Transfer the dichloromethane to a preweighed (50 ml)
Erlenmeyer flask. Carefully, evaporate the solvent on a steam batch and recover the camphor.
Calculate percent yield
Analysis: Take a melting point (172-174C)
Write your discussion on the back of this paper.