December 03, 2024, 04:34:21 PM
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Topic: Do carbocations only rearrange in acidic medium?  (Read 177 times)

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Offline Lateritious

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Do carbocations only rearrange in acidic medium?
« on: November 28, 2024, 10:42:18 PM »
I've always been under the impression that there is a driving force to rearrange to the most stable carbocation if possible but on my recent orgo 1 test I lost marks for saying that it would rearrange since it wasn't in an acidic medium(it was an SN1/E1 reaction involving a secondary alkyl halide undergoing solvolysis in methanol). I was wondering if anyone could explain why it wouldn't happen or help me find a way to explain/prove to my teacher that it would because I lost significant grades because of this.

Offline Babcock_Hall

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Re: Do carbocations only rearrange in acidic medium?
« Reply #1 on: November 29, 2024, 07:45:45 AM »
What kind of carbocation did you show as the product of the rearrangement, and how did the rearrangement happen in your proposed mechanism?

Offline rolnor

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Re: Do carbocations only rearrange in acidic medium?
« Reply #2 on: Yesterday at 04:27:35 PM »

It seems to me that you don't need an acidic medium to get rearrangement, but if you have the nucleophile in large excess, the substitution reaction will predominate. But I do think you will get some rearrangement in any case.

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