
Assessing for least basic nitrogen
Hi Folks,
This was a question from our last exam, which I got correct but I was close to selecting letter A.
Here is my thinking:
The lone pairs on B and D are not contributing to aromaticity and are therefore free to act as a source of electrons, this makes them more basic so we can eliminate these two options. Same situation for option A I guess, right?
The lone pair on C is contributing to aromaticity on this molecule, and is less available as a source of electrons (less available to act as a base).
What if we compared A to C and asked which is more acidic? Would C be more acidic because the conjugate base has resonance stabilization and option A does not?
Okay, thanks for your help!