Why is phenol more polar than alcohol? Why is phenol more polar than alcohol. I mean the benzene ring seems to be extremely unpolar. Furthermore, is the hydrogen bonding stronger in phenol than in alcohol? Are polarity and hydrogen bonding related (in hydroxy compounds)?

I am doing TLC and I was taught that hydrogen bonding can occur with the alcohol/phenol and that alcohol has stronger hydrogen bonding to the silica gel than it would have despite the lower polarity a lower Rf value than phenol.

But to be honest I am very unsure about those teachings.
The OH group of phenol is indeed more polarized - and a stronger acid - than the OH group of an aliphatic alcohol - maybe that is what you are asking. There are two contributions to this: 

(1) inductive: the sp2 hybridized carbon participating in the sigma bond to the OH group is more electron-withdrawing than the sp3-hybridized carbon of an alcohol bonded to OH; and 

(2) mesomeric: the phenyl group allows non-bonding electrons on oxygen to partially delocalize into the ring via pi bonding.