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chem262lexp6 - hydroxyl functional group is sp 2 hybridized...

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AtLee Watson Experiment 6: The Oxidation of Isoborneol In this experiment, isoborneol was oxidized to camphor using chromic acid (theoretically). However, the purified product was contaminated repeatedly due to a faulty hose and aspirator vacuum in the sublimation apparatus. No experimental product was obtained. However, an experimental product was obtained from a fellow classmate (Fletcher Mebane) and the melting point was determined to be 158 0 C- 174 0 C. The actual melting point is 175 0 C - 177 0 C. This large range in the melting point was primarily due to impure substances and water present in the purified product. 1. (TA working office hours Monday 4:00PM indicated that there was a change in the question from oxidation state to hybridization of C atom attached to –OH group and ketone group.) The hybridization state of the carbon atom attached to the hydroxyl group on Isoborneol before oxidation was sp 3 . After oxidation, the carbon atom previously attached to the
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Unformatted text preview: hydroxyl functional group is sp 2 hybridized. In both compounds the oxygen compound is sp hybridized, but in camphor there is a pi bond that contributes to the hybridization state. 2. A NMR can be used to provide evidence that camphor was formed because there was a hydroxyl group and an alkyl hydrogen located alpha to the carbon atom (from question #1 above). In the camphor product there is a ketone functional group attached to the same carbon. The hydroxyl group produces a broader peak than the ketone group, and also there is no peak for the non-existent alkyl hydrogen in the camphor sample that was present in isoborneol sample. 3. If no “cold finger” was used in the sublimation apparatus, then condensation would not have occurred because there was no source of lower temperature. Thus, no purified camphor product would have formed on the cold finger and melting point determination would not have been possible....
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