During lecture with our chemistry teacher, he randomly asked us to compare solubility of phenol and p-nitrophenol, we expected p-nitrophenol to have greater solubility than phenol due to better dipole moment (5.43 D which is 1.70 D for phenol) and better hydrogen bonding but as it turns out phenol is way more soluble (84 g/L) than p-nitrophenol (10 g/L). Teacher was also confused, he didn’t resolve the problem that day and came to class next day saying he did some research and has found the reason but he hasn’t disclosed it yet and has asked us to do research ourself to get the reason.
I think the reason behind this abnormal behaviour is the strong attractions already existing between p-nitrophenol molecules is a lot more stronger than interactions between water molecules and interactions with water molecules are weaker, I am not sure of my answer and would like a better explanation / ideas to think about solubility. What do you guys think should be the reason for this abnormality.