Fundamentals of Organic ChemistryChemistryGeneral Organic Chemistry
Which of the following compounds is the strongest base?
Correct answer
0
Step-by-step solution
The basicity of a compound depends on the availability of the lone pair of electrons on the heteroatom for donation to a proton. In compound (A) (piperidine), the nitrogen atom is sp^3 hybridized. The lone pair is localized and readily available for protonation. It acts as a typical secondary aliphatic amine. In compound (B) (tetrahydropyran), the heteroatom is oxygen. Since oxygen is more electronegative than nitrogen, it holds its lone pairs more tightly, making it a much weaker base than aliphatic amines. In com