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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sharbeldam on July 30, 2020, 07:50:59 AM

Title: Carbocation rearrangement question
Post by: sharbeldam on July 30, 2020, 07:50:59 AM

The question lies in the picture below, my first question is, can groups other than alkyl/hyride shift as well like this in the picture? it's not too large?
And if they can, why wouldn't the benzene ring shift instead since it's the smallest.
the teacher said the first product would happen but why? the carbocation wouldn't be as stable because NO2 is electron withdrawing and it would make the carbocation less stable...

Any explanation?

Title: Re: Carbocation rearrangement question
Post by: rolnor on July 30, 2020, 09:44:40 AM

You need to draw the mecanism to understand why p-methoxy but not p-nitro can rearrange this way.

Title: Re: Carbocation rearrangement question
Post by: sharbeldam on July 30, 2020, 09:50:49 AM

So this is not normal shift? like not same mechanism as hydride/methyl shift?
If not, any link for the mechanism?

Title: Re: Carbocation rearrangement question
Post by: sharbeldam on July 31, 2020, 05:19:04 AM

anyone has a link for the suggested mechanism that shows that only activating groups can rearrange?