[Juicebox]

Hello, I need help with the problem below. I'm at a loss on how to expand the ring while retaining the "tent-post" methyl group.

[g-bones]

Its important to look at your molecule and imagine which portion will attack the proton.  in addition drawing out intermediates and resonance structures will offer the solution.  its worth reviewing E1 and SN1 type reactions. 

[Juicebox]

Am I right in thinking that I should be going for a carbocation intermediate followed by a 1,2-methyl shift? If so, I cannot figure out how to accomplish that. If not, I'm equally lost.

Thanks for the tips so far, I'll keep trying.

[orgopete]

The suggestion of g-bones is very good. Perhaps it might help to tell you that this is an equilibrium reaction. The product could reform the starting material from the same intermediate. What is the intermediate?

[Juicebox]

Alright, I've never dealt with a proton like this before, and I'm not sure I have the answer. My solution has the hydrogen cation in solution deprotonating the "tent-post" methyl group (this is the step I'm uncertain of, I've never seen that before), producing a carbocation which undergoes a 1,2-methyl shift to produce a resonance stabilized cation. From there I just need to protonate the cation, I'm not sure if there would be any issue of using the hydrogen gas I generated earlier.

Thanks again for your guys' help so far!

[Doc Oc]

Not correct.  Very, VERY not correct.

You have an acid catalyst and a Lewis base in the molecule.  Start there.

[Juicebox]

Haha, alright I'll start over. I think I want to cleave the ether first, that's where I will start.

Edit: Alright, I think I have the correct mechanism now:

[g-bones]

your last reaction mechanism seems to be reasonable.  be careful, though, remember that arrows reflect the movement of electrons and since your are dealing with a proton in your first step (which has no electrons) you should reconsider which electrons are forming the O-H bond.

[Juicebox]

Ah, yes of course, my mistake.

Thanks for everyone's help.

[Doc Oc]

That's MUCH better, nice work.