Can anyone explain this increasing basicity trend?
Pheno l< Ethanol < isopropyl alcohol< tert butyl-alcohol
Thanks!
i'm not sure if this is the correct way to look at it. But this is how I got this question.
Instead of basicity, I thought of it in terms of strength of conjugate acid.
Phenol is the strongest acid of the group because after it gives up its proton in aqueous solution, its negative charge can be stabilized by delocalization around the aromatic ring.
the next 3 can be thought of in terms of being a primary alcohol, secondary, and tertiary alcohol. A positive charge on a tertiary alcohol is the most stable carbocation. However, a negative charge on a tertiary alcohol is the least stable, which is why I would place it at the very front, and label it as the weakest acid, or strongest base. The reason why a tertiary alcohol is the least stable is because alkyl groups are activators, and donate electrons into the ring. This destabilizes the charge. (Remember, deactivators such as Halogens, and NO2 will withdrawl electrons from the ring, and thus stabilize negative charges). Therefore, having more activators (alky substituents) will make the negative charge increasingly less stable, and thus more basic.
I hope that helped, if not, let me know and I'll try to make it more simple.
