I am doing some exam preparation and I came across this Question which I am finding challenging:
List from least polar to most polar, the following molecules:
Naphthalene, Phenol, 3-aminophenol and chlorobenzene.
I believe I know that Naphthalene is least polar as the benzene ring is very stable however, the confusion arises with chlorobenzene as the substituent Chlorine is very electronegative hence, it is strongly inductively electron-withdrawing thus is less polar than a simple benzene ring. So which is less polar, chlorobenzene or naphthalene?
Also which is most polar? 3-aminophenol or phenol? Phenol has a lone pair on oxygen in the oH group which can donate electrons to the ring, although with 3-aminophenol, both the NH2 and OH donate electrons, so wouldn't 3-aminophenol be more electron rich and hence more polar?
Please give the order of the molecules from least to most polar, explaining the order itself.