[theanonymous]

So for the first reaction, usually when I get a problem like this, he molecule is being treated with something like H-Br, so that tI can first protinate the OH on the alcohol, and then do the rest no problem... However, this one looks more compliacted with the "EtO^-/EtOH" thing at the top of the arrow.

I don't know what to do first! *delete me*!!

[Babcock_Hall]

Use the base to remove a proton from your alkyl bromide.

[Dan]

Hint: You will have to draw these molecules in boat chair configurations to understand the regioselectivity and rate differences.

Edit: Boat/chair mix-up corrected

[mamid]

Draw the structures in CHAIR configuration so that both bromine and the anti-H on the neighbouring C('s) are axial (conformation necessary for concerted elimination). What (how many) conformations are possible in each case?

[orgopete]

Hint, since eliminations are fastest when the groups are anti. For a ring, the leaving group should be axial. Draw the conformers with axial bromine atoms, and compare which protons are anti.