Q7_14 - Questions from Email “I had a question on...

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Unformatted text preview: Questions from Email “I had a question on the homework from chapter 7: On #14, isn't neopentyl alcohol, (CH3)3 ­C ­CH2OH, a primary alcohol? If so, why does the solutions manual have it going through an E1 mechanism to form 2 ­methyl ­2 ­butene, where the protonated hydroxyl is removed by itself rather than because of the formation of a double bond from the removal of the beta hydrogen like in an E2? Thanks!” We have talked about how primary carbocations are unstable and that they rarely form. You can think about this mechanism in two different ways. 1) The mechanism they give in the solutions manual is really giving a step by step electron pushing mechanism for each distinct bond making a breaking that happens going from starting material to final product. 2) However, that doesn’t necessarily mean that some of the bonds being made and broken aren’t actually being made and broken simultaneously. That is what the solutions manual means by “steps 2 and 3, ionization and rearrangement may occur simultaneously” Given what is known about primary carbocations, this is most likely what is actually happening in real life. Please see the attached document for structural visualization. ...
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