Isoborneol With Bleach

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Experiment VI: Oxidation of Isoborneol with Bleach

Purpose: In this experiment, Green chemical procedures were applied to oxidize isoborneol to camphor using bleach (NaOCl), rather than the tradition chromium-based oxidizing reagents. The camphor was then purified using the process of sublimation.

Procedure: Using a 50-mL Erlenmeyer flask, 1.316 g (8.5 mmol) isoborneol and 1.0 mL (17 mmol) glacial acetic acid were stirred vigorously with a magnetic stir plate. A volume of 1.7 mL NaOCl was added to solution, and it was then heated to 50° C. Drop-wise, 15 mL of NaOCL were added to the solution over the following 10 minutes. The solution was heated at 70° C to maintain a temperature of 50° C. When it momentarily reached 55 ° C it was placed in an ice bath until it was 50° C again. The solution was then heated at 65 ° C for the remainder of the reaction. Over the next 20 minutes, the presence of NaOCl in the reaction mixture was ascertained every 5 minutes using a starch-iodide test. If the test was negative, additional NaOCl was added to achieve a positive test (0.5 – 1 ml fractions). After 20 minutes, the reaction mixture tested positive for NaOCl, and NaHSO3 was
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One other type of spectroscopy that would be particularly useful for determining the success or failure of my reaction would be infrared spectroscopy. IR spectroscopy measures the absorption of IR light by chemical bonds.1 The isoborneol would produce an IR absorption band around 1260 – 1000 cm-1 (due to the C-O bond) that would not be present in the IR spectrum of camphor.1 Conversely, camphor would produce an IR absorption band around 1760 – 1670 cm-1 (due to the Carbon-Oxygen double bond of the ketone group) that would not be present in the IR spectrum of isoborneol.1 By identifying the absence of the C-O absorbance band and the presence of the Carbon-Oxygen double bond absorbance band in an NMR spectrum, I would be able to conclude that isoborneol was successfully oxidized to

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