Orgo Unit 7.2 Discussion

Orgo Unit 7.2 Discussion - the unstable positively charged...

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Propose a reason(s) for tertiary alcohols being unreactive with most oxidizing agent According to our textbook, when molecules undergo oxidation reactions, these will closely resemble the mechanisms as demonstrated in E2 reactions. Therefore, let’s review what occurs in such reactions. In section 12.12 of the textbook, we see that the E2 reaction begins when a base attacks a hydrogen molecule on the carbon that neighbors the carbon carrying the leaving group. As the hydrogen is attacked, an alkene double bond is formed, and the leaving group starts to depart from the molecule simultaneously. Now, let’s examine the mechanism of oxidation reactions for a primary alcohol such as what is shown on page 522. In the reaction of the primary alcohol with the CrO3 oxidant, a chromate intermediate is formed. A base then removes the hydrogen that is bonded with
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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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