Comments on: Elimination (E1) Reactions With Rearrangements https://www.masterorganicchemistry.com/2012/11/09/e1-reaction-rearrangement/ Thu, 07 Dec 2023 23:03:36 +0000 hourly 1 https://wordpress.org/?v=6.6.2 By: Introduction to Rearrangement Reactions | Straight A Mindset https://www.masterorganicchemistry.com/2012/11/09/e1-reaction-rearrangement/#comment-679075 Thu, 07 Dec 2023 23:03:36 +0000 https://www.masterorganicchemistry.com/?p=6667#comment-679075 […] Elimination (E1) (See post: Elimination (E1) With Rearrangement) […]

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By: James Ashenhurst https://www.masterorganicchemistry.com/2012/11/09/e1-reaction-rearrangement/#comment-564524 Thu, 19 Sep 2019 16:46:38 +0000 https://www.masterorganicchemistry.com/?p=6667#comment-564524 In reply to Sina riahi.

Hydride shifts, generally, will perform 1,2 shifts much faster than alkyl shifts. First, think about the driving force for a 1,2 shift. The driving force is formation of a less substituted carbocation. If you have a secondary carbocation adjacent to a tertiary carbon, and the tertiary C-H migrates, you obtain a (more stable) tertiary carbocation. However if an alkyl group migrates, you obtain an (equally stable) secondary carbocation.

Exceptions can occur. In the lab, there are cases where 1,2- alkyl shifts will happen preferentially, especially in rigid cyclic systems. In rigid, cyclic systems containing a free carbocation the groups likeliest to migrate are those which have their bonds aligned with the empty p-orbital; axial groups, in other words. See the references at the end of the post for some examples.

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By: Sina riahi https://www.masterorganicchemistry.com/2012/11/09/e1-reaction-rearrangement/#comment-564498 Thu, 19 Sep 2019 11:16:31 +0000 https://www.masterorganicchemistry.com/?p=6667#comment-564498 Hi , thanks for your great post, i am 16 but i love chemistry and i am going to paticipate in IChO.but a question, if both alkyl and hydrid shift is possible, what will happen?

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