How does pKa affect equilibrium?
To be sure, its magnitude is inversely proportional to the amount of dissociation the acid undergoes in solution.
Consider a reaction,
We can look at this from a perspective of the magnitudes of
The latter is far more likely to dissociate in this solution, and hence, the equilibrium will probably favor the left.
In non-scientific language (which helped me more during organic chemistry): the alkane is happy with its proton, but the phenol isn't.