Why does the nitrogen atom in pyridine () act as a much stronger Lewis base than the nitrogen atom i — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

In pyrrole, the nitrogen lone pair must participate in the $\pi$ -system to achieve the $6\ \pi$ -electron aromatic state, making it unavailable as a base. In pyridine, the aromatic sextet is provided entirely by the carbon-nitrogen double bonds; the lone pair resides safely in an orthogonal $sp^2$ orbital, free to act as a base.