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262-6 - Anusha Vadlamudi TA Lindsay Aldridge Chem 262 L 401...

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Anusha Vadlamudi TA: Lindsay Aldridge Chem 262 L 401; Rm: 300 Experiment VI: The Oxidation of Isoborneol To a 10 mL Erlenmeyer flask, 0.356 g isoborneol was added along with a stir bar and 1 mL acetic acid. When the acid was added the isoborneol dissolved. The solution was heated gently. At about 50 degrees Celsius, 2 mL chromic acid was added dropwise. The temperature was kept below 60 degrees Celsius by placing the flask in ice water for about 20 seconds to cool it. After 15 minutes the mixture was poured into 25 mL ice water. The product was filtered by suction using a water aspirator. A sublimation apparatus was set up and an aspirator vacuum was used to sublime some product. Melting points were measured before and after the sublimation. The crude product looked slightly grey compared to the bright white pure product. The melting point of the crude sample was 154°C -163°C and that of the pure sample was 167°C -175. This was rather close to the literature mp value of 177, indicating purity. Questions 1) The hybridization state of the carbon atom bonded to the hydroxyl group in isoborneol
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