Rank the nitrogen atoms in chloroquine,shown below,in order of decreasing basicity,putting the most basic nitrogen atom first.

Question

Quizplus · Accepted Answer

The basicity of a nitrogen atom is determined by its ability to donate a lone pair of electrons. In chloroquine, N3 forms a double bond with the quinoline ring, which reduces its basicity. Therefore, N1 and N2 are expected to be more basic than N3. Between N1 and N2, N1 is attached to a more electronegative atom (oxygen) than N2, making it more electron-donating and hence more basic. Thus, the correct order of decreasing basicity is N3 > N2 > N1, which matches choice C.

Rank the Nitrogen Atoms in Chloroquine,shown Below,in Order of Decreasing