Experiment Two: Bleach Oxidation Of Isoborneol

Experiment TWO: Bleach Oxidation of Isoborneol Reaction (15 pts) –accurate drawing with ChemDraw Procedure
Isoborneol (1.32 g, 8.5 mmol), NaOCL (1 mL, 7.6 mmol), and acetic acid (1.7 mL) was vigorously stirred in a flask. The solution was then heated to 50°C. NaOCl (15 mL) was added dropwise to the solution over a 10 minute time period. Parafilm was then used to seal the flask, while being stirred and heated (50°C). Samples of the solution where taken every 5 minutes and subjected to a starch-iodide paper to check for excess NaOCl. Once the test produced positive results (purple color), a minimal amount of saturated NaHSO3 was then added to the solution to produce a negative test. The solution was then cooled by a ice-water bath.

Camphor is produced by oxidizing a secondary alcohol, isoborneol, into a ketone. The melting point of the product was experimentally determined to be 169°C. Comparing 169°C litature value of 174-179°C, it can be assumed that the product was not completely purely.1 To improve purity, procdure could be examined. Allowing the reaction more time to occur, along with more through filtering may increasing purity. Additionally, the heating during sublimation could be done slowly inorder not to burn the product. The mass of the crude product was 0.77 g, where the purified product was 0.03g. Comparing the pure product to the amount of isoborneol used, the percent yield was found to be 2.4%. To improve this low percent yield the procedure should be again be examined. Reducing the amount of product lost during transfers, filtration, and sublimation would improve yield. Better transfer would involve more through washes of glassware. Moreover, the yield of the sublimation process was very low (3.9%). To address this issue more time should be allotted for the product to collect on the cold finger. To further examine the purity and identity of the produced specie(s), mass spectrometry, gas chromatography, and NMR could be considered. Understanding what the impurities found in the reaction are may offer insight as how to improve the

Considering that the reaction was done a micro scale the amount of waste is limited (Prevention #1). Bleach was used in this reaction instead of a chromium compound. Bleach is less hazardous in comparison, therefore less hazardous chemical syntheses (#3) was followed. Consider that all waste can be safely disposed with merely water, and that the chemicals used are at most irritates, then potential for harmful chemical accidents is limited (Inherently Safer Chemistry for Accident Prevention #12).
2. Consider that sublimation involves the transition of a solid to a gas. Iodine will exist was a solid where Bromine will not. Molecules of iodine will experience a strong intermolecular forces, London dispersion, due to the location of location of its electrons. Bromine will experience weaker forces, considering the electrons are closer to the nuclei (consider the small atomic radius compared to iodine.
3. Consider that the difference between the reactant and product’s NMR spectrum will differ due to the change of the an 2o alcohol to a ketone. Isoborneol would there for have two more speaks than what would be seen in the camphor spectrum. These peaks would include a single peak from the OH proton along with a peak from the proton found on the carbon that that OH group is attached (approx. 3.5 ppm). Camphor would lack this two protons, thus causing smaller splitting patterns than would be seen in the isoborneol