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Results and Discussion-Camphor

Results and Discussion-Camphor - the transfer of the reflux...

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Results and Discussion We began our experiment by measuring out .205 grams of Camphor and .105 grams of NaBH4. Each addition of the NaBH4 caused the mixture to fizz. The mixture was slightly opaque at the conclusion of the reflux. The precipitate formed immediately when adding it to the cold water. After suction filtration, we collected 0.100 grams of white crystals giving a percent yield of 48.3 percent. The IR spectrum looked as we had expected. There was an absorption around 1090, indicating a carbon-oxygen bond. It contained a broad/intense absorption around 3400, indicating an alcohol was present. There was also a strong absorption of 3000 indicating hydrogens on sp3 hybridized carbons. Conclusion Our percent yield was slightly low. This may have been due to the loss of product during
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Unformatted text preview: the transfer of the reflux mixture to the beaker. We were not able to determine whether our product contained any impurities (no determination of melting point). Questions 1. Why is the major product of this reduction isoborneol and not borneol? The major product is isoborneol because of steric hindrance caused by the methyl groups on the bridge of the molecule. This steric hindrance keeps the sodium hydroboride from attacking the carbonyl carbon from the top face. This reaction proceeds slower than the nucleophilic attack on the bottom face of the molecule so less borneol is formed. 2. Starting from camphor, provide a multi-step synthesis that would favor borneol over isoborneol....
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