[mintyrogue]

Hi, I was wondering how to convert 1-methylcyclopentanol into 2-methylcyclopentanol (no solvents are given for this question, I'm assuming we can approach the question with any solvent as needed).

I know that 1-methylocyclopentene is an intermediate for this reaction, but I'm confused with the elimination portion.  What would be the leaving group for this reaction?  I know that OH- and CH₃⁺ are both bad leaving groups since they're both unstable.  Should there be some sort of protonation to convert the alcohol group into OH₂?

Thank you in advance!

[phth]

If pronation (ROH2+) occurs is the mechanism E1 or E2?

[orgopete]

I think you need more steps.

[AromaticAcrobatic]

There will always be a proton transfer step when hydroxyl is the leaving group. Oxygen isn't just gonna leave. A good comparison would be hanging out a party, talking to a cute girl. Your chilling, having a good time, helping your friends, your friends are helping you, your not just gonna leave. But if you find out the girl your most interested in has slept with pretty much everyone at the party and then some one slips and spills cranberry vodka on your new periodic table shirt your gonna leave. Oxygen is the same way he's not gonna leave unless he's pissed. Protonating oxygen( giving him the + charge) makes oxygen very unhappy, unhappy to the point where he will just leave. (Understandable, I would be bummed if the girl I was really into slept with everyone at the party and then some one ruins my periodic table shirt)

Mechanistically and synthetically, think Zeitsev followed by Anti-Markov.
Hope this helps!