[eglaud]

So lets say we have an alcohol bonded to a carbon that is doubly bonded to another carbon on, say, a pentene molecule. What i'm curious about is the mechanism that creates a ketone here. Does the double bond shift onto the oxygen, and a hydrogen somehow attaches to the carbocation that is created? Or does the oxygen's lone pairs create a double bond and the already existing double bond move onto the carbon, creating an anion that attracts a hydrogen? Or is it neither? I've just realized I've been writing out this reaction a bunch, but I don't know where the double bond comes from here. Any information here would be great, thanks.

[Babcock_Hall]

What you are describing sounds more like a ketone-enol equilibration.  Both acids and bases can catalyze such a process.

[eglaud]

Right, I just looked that up and it answered my questions - thanks!