Problems and exercisesPyridine and six-membered heterocycles
Exercise 1
Rank by basicity: pyridine, piperidine, pyrrole and 4-dimethylaminopyridine (DMAP). Explain why DMAP is more basic than pyridine and why it is protonated on the ring nitrogen and not on the dimethylamino nitrogen.
Exercise 2
Propose a synthesis of 4-aminopyridine and another of 2-aminopyridine from pyridine. Why does 3-chloropyridine not react with sodium methoxide under the conditions in which 2-chloropyridine does?