[Lateritious]

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.

[Babcock_Hall]

What kind of carbocation did you show as the product of the rearrangement, and how did the rearrangement happen in your proposed mechanism?

[rolnor]

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.