acids and bases

Question

why 2-methyl pyridine is a stronger base than pyridine?

Answer 1

2-methyl pyridine is a stronger base than pyridine because of it's conjugate acid stability. If we were to have both 2-methyl pyridine and pyridine act as a base and look at their conjugate acids, we see that they will both carry positive charges on the nitrogen atoms once protonated. Both bases retain their aromaticity, however, 2-methyl pyridine has a resonance structure where we flip the electrons of the double bond between the nitrogen and carbon two onto the Nitrogen atom, which alleviates the positive charge on the nitrogen and places it on C2, which is tertiary, and more stable than if we used pyridine, which would have a secondary carbocation. So, the more stable the conjugate acid, the stronger the initial base (similarly the way we compare acidities with acids and conjugate bases).