why are phenols less soluble in water than other alcohols

It's because the oxygen s electrons in the p orbital delocalise into the ring, this reduces the phenols ability to make hydrogen bonds, which is what solubility in water is about
the oxygen uses lone pairs to make h bonds

The phenyl ring is also much more hydrophobic than say, an ethyl chain.

Oh right, so does the same concept apply to carboxylic acids i.e. the longer the chain the lower the solubility due to an increase in the length of the hydrophobic region of the acid?

Oh right, I was only thinking about the hydrogen in the OH group in phenol Correct me if I'm wrong, but from your post are you saying that the oxygen in phenol can not hydrogen bond with water as well. What about the hydrogen, they're not affected right and can still bond with water, right?

Oh right, I was only thinking about the hydrogen in the OH group in phenol Correct me if I'm wrong, but from your post are you saying that the oxygen in phenol can not hydrogen bond with water as well. What about the hydrogen, they're not affected right and can still bond with water, right?

The oxygen is unable to for h- bonds with hydrogen atoms of water molecule due to delocalization of electrons and therefore phenol is only partially soluble cuz the hydrogen of oh group in phenol do form the h- bonds, plus the benzene ring is an hydrophobic group which further contributes towards lesser solubility

Logically it sounds like a phenol should be highly soluble in water.

The benzene ring surely heavily deprives hydrogen atoms of electrons and makes them extremely susceptible to forming hydrogen bonds with oxygen in water.or does the high electron concentration to some extent repel the oxygen and either weaken its bonds with hydrogen or prevent the from happening.

Such a bizarre subject aha

So the benzene ring is non-polar?

The delocalised ring consists of one electron from each carbon atom, but the carbon atoms have 4 electrons each, so the delocalised ring doesn't steal electrons from the C-H bond (if that's what you mean), the carbon-hydrogen bonds are unaffected by the delocalised ring. The benzene ring is non-polar as the overall dipoles cancel each other our. Non-polar parts of a compound can not form hydrogen bonds with polar water molecules. Hope this helps I was a little confused myself

So the benzene ring is non-polar?

That's a really awesome reply thanks mega helpful

Benzene is non-polar. Based on the STRUCTURE you have a very symmetrical compound of just carbon and hydrogen and any dipoles formed by the C-H are all counteracted by each other resulting in a net zero dipole. The main ring are all composed of bonds of the same element, Carbon which makes that bond virtually non-polar. Sure, there is a pi electron cloud which essentially hovers the entire ring and because of symmetry again, benzene is non-polar.

Based on its PHYSICAL Property - like solubility, it is soluble in other non-polar compounds LIKE hexane, etc and NOT soluble in a Polar solvent or substance like WATER.

I hope you are not confused now. So you see sometimes you can explain away based on just structure, sometimes thru its physical properties or chemical reactivities.