Chance P.

asked • 10/10/23

Proposing mechanisms for carbocation rearearrangements involving hydride or alkyl shifts

For each in the attached image,

https://ibb.co/6W8Hdw2

how can I draw plausible mechanisms for carbocation rearrangements involving hydride or alkyl shifts, where the carbocations can undergo rearrangements to form more stable ions by the transfer of a hydride ion or alkyl group?

1 Expert Answer

By:

Chance P.

Thank you. So for (b) 2-methylbutane there would be an alkyl shift correct? The carbocation would shift to the 2nd carbon position?
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10/13/23

William C.

tutor
For (b) you get: (CH₃)₂CH–⁺CH–CH₃ → CH₃)₂C⁺–CH₂–CH₃ which is a hydride shift converting a 2° carbocation to a more stable 3° carbocation.
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10/13/23

William C.

tutor
(CH₃)₂CH–⁺CH–CH₃ → CH₃–⁺CH–CH(CH₃)₂ is what an alkyl (CH₃) shift would look like. You just get back the same 2° carbocation you started with.
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10/13/23

William C.

tutor
See wyzant.com/resources/answers/934135/drawing-of-mechanisms-for-carbocation-rearrangments-involving-hydride-or-al where I did the mechanism for part (b) for someone else's question.
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10/13/23

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