Question

Imidazole is a commonly used base in organic chemistry. While imidazole contains two nitrogens, only one of them is significantly basic. Using your chemical intuition, predict the more basic nitrogen.

Answer 1

Answer:

See explanation and image attached

Explanation:

The structure of imidazole is attached to this answer. The compound is colourless. The solid can be to dissolved in water leading an alkaline solution. Owing to the fact that imidazole possesses heteroatoms in an aromatic heterocycle it is classified as a diazole. The nitrogen atoms in imidazole are not adjacent to each other.

From the structure shown, we can see that the lone pair of the sp2 hybridized nitrogen atom is available because it is not part of the aromatic system of the heterocycle. This nitrogen is much more basic than the nitrogen atom attached to hydrogen whose lone pair becomes part of the aromatic sextet hence it unavailable for protonation and less basic.