N,N-diethyl-m-tolumide (DEET) is the active ingredient in many mosquito repellents. What is the hybridization state of the nitrogen atom in the structure of DEET shown below

Question

Quizplus · Accepted Answer

The nitrogen atom in DEET has a lone pair of electrons, indicating that it is sp3 hybridized. However, it also has a resonance structure where the lone pair can be delocalized onto the neighboring carbonyl group, making the nitrogen atom sp2 hybridized. The correct hybridization state is an average of these two, which is sp³.

N,N-Diethyl-M-Tolumide (DEET) Is the Active Ingredient in Many Mosquito Repellents