Question

How do we compare the acidities of `Et_3SiOH` and `"methanol"`?

Answer 1

Well, `pK_a` might be a convenient means of comparison........

Explanation:

While these are estimated values `pK_a` for `Et_3SiOH` is given as `13.6` versus `15.5` for methanol - given the logarithmic scale that is 2 orders of magnitude. The larger, more electropositive silicon atom is better able to stabilize the negative charge.