Madison McVeyCHEM 237 – 549December 5, 2016Oxidation of Secondary Alcohol Lab Report The purpose of this experiment was to investigate the oxidation reaction of a secondary alcohol to a ketone product and identify the starting material of the reaction. Distillation techniques and Infrared spectroscopy analysis will be used to determine the identity of the compound. The weight of the reaction flask was 45.168 g to begin with, and when the reaction solution was added, weighed a total 46.555 g. When the addition of bleach was complete, the starch iodide test was performed and determined to be positive. Excess oxidant was destroyed with a small addition of sodium bisulfate and another starch iodide test completed and determined to be negative, as desired. The pH of the solution was tested using pH paper and sodium hydroxide was added until the solution was at a pH of 6-8, which ended up being about 2 mL. This was the only unexpected event to occur, as the solution ended up being a bit too basic when tested a second time. The TA checked the solution and said that it was fine to continue. The solution was transferred to a separatory funnel and dichloromethane was added to the solution. The aqueous solution was extracted and the separatory process repeated. Potassium carbonate was then used to dry the solution and form asolid carbonate that then dried for 10 minutes. A simple scale distillation set up was then assembled and the process completed. The remainder of the dichloromethane was extracted at its boiling pointof about 40*C and the remainder of the solution distilled at approximately 65*C. Taking the product collected after the distillation of dichloromethane, an IR spectrum was obtained and analyzed. When compared to the standards, it was determined our alcohol starting product was cyclopentanol and our ketone result was cyclopentanone. The IR spectrums obtained are attached to this report. The similarity between the spectrums obtained confirms that the experiment was successful and a secondary alcohol was in fact oxidized to a