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Unformatted text preview: the unstable positively charged oxygen molecule. Another base attacks and removes a proton from carbon bonded to the oxygen atom. As this occurs, a carbon-oxygen double bond begins to form and the CrO3 leaving group prepares to depart, simultaneously. What is different among tertiary carbons is that no atoms can be removed in the reaction such that the carbon-oxygen double bond can form. Our only option would be to break carbon-carbon bonds for this to occur, but that is unlikely due to their stability. As Michael pointed out, it may be worthwhile to simply consider what an oxidation reaction exactly entails. In our case, it would be the loss of hydrogen molecules, which in turn would allow a double bond to be formed. Oxidation cannot occur in tertiary alcohols because we do not have sufficient hydrogen atoms to remove from the molecule....
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- Spring '11