Synthesis Of Ketone Lab Report

Courtney Smith Organic Chem. II Lab
February 29, 2016
Synthesis of Camphor
Koeck

Abstract
Within this experiment, one is oxidizing a secondary alcohol, isoborneol, to a ketone, called camphor. In order to purify the camphor, sublimation is performed due to the fact that camphor changes from a solid to a vapor when heated. To measure the purity of the camphor sublime, the melting point is measured. As a result, the camphor sample will have a melting point ranging between 179 ºC to 212 ºC.
Introduction
Camphor is a ketone that is found in the evergreen plant, cinnamomum camphora. The substance is waxy with an odor. The medicinal use of camphor has been utilized for centuries. Camphor has been used to relive a cough; the substance can be found

The advantages of using sublimation is due to the fact that no solvent is required and keeps the loss of the substance to a minimum (Lehman, 2009).
Methods & Materials
The following experiment procedure was followed according to Multiscale Operational Organic Chemistry (Lehman, 2009). One will begin the oxidation reaction of isoborneol by combining 3.86 grams of isoborneol with 2 mL of glacial acid, then adding 4.4 mL of bleach to the flask. In a separtory funnel, add 40 mL of bleach to the funnel; then add the bleach from the funnel into the flask over a 10-minute period with continuous swirling. Once complete parafilm the flask and mix for 30 minutes. During this 30-minute period test the reaction for excess hypochlorite by using starch- iodide paper.
After the reaction is complete, cool the mixture to below 5 ºC and then collect the product via vacuum filtration. Then dry the product at room temperature, weigh and measure the melting point. Lastly, one will purify the product via sublimation and once complete measure the melting point.

Meniscus Temp. Melting Point
3.860 g 1.925 g 186.6 ºC 190.2 ºC 193.8 ºC

As a result, one may conclude that experiment was successful and the substance was purified. The final percent yield was measured to be approximately 49.87 %. The melting point of pure camphor is 179 ºC and isoborneol is measured at 212 ºC.
Discussion
According to the results, the isoborneol was able to oxidized to the ketone, camphor. The melting point of the product from the sublimation can be determined to be purified camphor. One can potentially be concluded that the camphor was synthesized but since isoborneol can also be sublimes in elevated temperatures, the camphor product may contain some residual isoborneol affecting the final melting point to be higher than expected.
Conclusion
In conclusion, isoborneol was oxidized into a ketone and then purified via sublimation. The final percent yield was approximately 49.87%