Question 8.11: Combining Valence Bond and MO Theory Acetamide (C2H5NO), an ...
Combining Valence Bond and MO Theory
Acetamide (C_{2}H_{5}NO), an organic compound that has been detected in interstellar space, has the following connections among atoms and can be drawn using two nonequivalent electron-dot resonance structures. Draw both, and sketch a π molecular orbital showing how the π electrons are delocalized over the oxygen and nitrogen atoms.
STRATEGY
Draw the two electron-dot structures in the usual way (Section 7.9), including all nonbonding electrons. The two structures differ in that one has a carbon-oxygen double bond and a lone pair on nitrogen, while the other has a carbon–nitrogen double bond and an additional lone pair on oxygen. Thus, a π molecular orbital corresponding to the O-C-N resonance includes all three atoms.
