Question 5.6: Combining Valence Bond and MO Theory Acetamide (C2H5NO), an ......

General Chemistry: Atoms First [1015060]

Combining Valence Bond and MO Theory

Acetamide ( $C_2H_5NO$ ), 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 resonance structures in the usual way (Section 4.7), including all nonbonding electrons. The two structures differ in that one has a C=O double bond and a lone pair on nitrogen, while the other has a C=N 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.

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