o chem Q: methyl shift rearrangement

[Ryltar]

Methyl shifts only occur in carbocation forming reactions (E1, SN1), where there are no hydrides available for a shift to form the more stable carbocation. So instead a methyl shifts in this case. Correct?

---

Members don't see this ad.

 

[kov82]

well I could be wrong, but the whole point of the shift is to create the most stable carbocation possible, so that means if a methyl shift can happen AND it will create the most stable carbocation thats what will happen, if a hydride shift will create a tertiary carbocation then thats what will happen, you just have to know that 3>2>1 (and that you cant move a methyl or hydrogen from just anywhere) and you will know what to do automatically. Its not about choosing between the two, its about which will create the most stable conditions. I hope I understood your question correctly

 

[Ryltar]

That sounds right, thanks. I was just unfamiliar with methyl shifts considering I had o chem 3 years ago. DAT destroyer didn't have any example problems of methyl shifts unfortunately, which were popping up in ACS organic chemistry problems.

I guess the intent of my question was if say you can form the equivalent stability carbocation with either a hydride shift or a methyl shift, which would be the major product? I would assume hydride shift, because it would occur more rapidly due to less steric hindrance.

I probably don't need to worry about a question like this on the real DAT, but I'm just curious...