[electronuc]

So i can't figure this out.
There aren't any resonance forms to stabilize one more over another. Which is a better leaving group? (I know that alkoxides are strong bases - poor leaving groups)
Can it be that the higher substituded alkoxides are less stable because there are more electrons that destabilizes the negatively charged anion?

[electronuc]

I mean methoxide and not methyl oxide, was tired when I wrote the first post.. -_-

[Babcock_Hall]

I am not sure what you are asking.  You might compare the pK_a values of methanol, ethanol, and tert-butanol, as a starting point.

[electronuc]

I am not sure what you are asking.  You might compare the pK_a values of methanol, ethanol, and tert-butanol, as a starting point.

Thanks! What I've learned now is that methanol is more acidic in solution than an alcohol with more branching due to solvation.
So, methoxide would theoretically be a better leaving group than a bigger alkoxide as it will be more stable in a solution.

I was trying to rank how fast a reaction would be for the same compound but with different alkoxides as leaving groups.
I first assumed that an electric effect played a part in the stabilty of ionic compounds.