carbocation shift

[monsieurwise]

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Hi everyone!
I am a little confused about the carbocation shift. I know in my probrems, the H and the carbocation (+) sign would switch place when they are next to each other if that create a more stable carbocation. But can a whole group like CH3 switch place like H too? And can it be done multiple times until the carbocation find the stablest place to stay or only once?
Thanks guys!!

 

[aznnytezx]

Alkyl shift are the last resort one, it first does a hydride shift if they see the carbocation really unstable. If there are NO hydrogens to do the shift, then we start using alkyl groups because this would be a tertiary carbon.

With that being said, remember that alkyl group can do this because they are electron donating via hyper conjugation.

 

[monsieurwise]

Thanks =). So can this be done multiple times? For example shift from 1° to 2° and then 3°? Thanks you =)