Chemistry Stack Exchange is a question and answer site for scientists, academics, teachers, and students in the field of chemistry. It only takes a minute to sign up.
Sign up to join this community
If the hydroxl group on 4-aminophenol was protonated by a strong acid in aqueous solution, and the compound further to that dehydrated, could a rearrangement of the subsequent carbocation lead to formation of 2,5-cyclohexadien-1-imine and thus regenertion of the strong acid before SN1 was possible?
Is there a more common name for this sort of reaction (assuming it is possible)?
TL;DR
No
Explanation
As far as I understand, the reaction being suggested is as follows:
The first thing one should notice is that 2,5-Cyclohexadien-1-imine is not going to stay as it is. It will tautomerise to the more stable and aromatic aniline.
Let us go back to the starting material - 4-aminophenol. Both the oxygen and the nitrogen are directly attached to the aromatic $\pi$-system. Both can donate a lone pair and cause a +R effect. Their electronegativities would result in a -I effect, which is very small, compared to the +R effects. The point is, the starting material is electron-rich, i.e. nucleophilic. It would not leave a carbocation (if it does form) alone.
Also, the thing about the lack of a hydride donor...
