Drawpictorialrepresentations (as in Figures16-4 and 16-6) for the three bonding MOs and the two nonbonding MOs of cyclooctatetraene. The antibonding MOs are difficult to draw, except for the all-antibonding MO.
Classify the following compounds as aromatic, antiaromatic, or nonaromatic.
(c) 
(d) 
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Key Concepts
Aromaticity
Antiaromaticity
Nonaromatic Compounds
Make a model of cyclooctatetraene in the tub conformation. Draw this conformation, and estimate the angle between the p orbitals of adjacent pi bonds.
One of the following compounds is much more stable than the other two. Classify each as aromatic, antiaromatic, or nonaromatic.
a. Use the polygon rule to draw an energy diagram (as in Figures 16-5 and 16-7) for the MOs of a planar cyclooctatetraenyl system.
b. Fill in the eight pi electrons for cyclooctatetraene. Is this electronic configuration aromatic or antiaromatic? Could the cyclooctatetraene system be aromatic if it gained or lost electrons?
Classify the following compounds as aromatic, antiaromatic, or nonaromatic.
(a)
(b)
Does the MO energy diagram of cyclooctatetraene (Figure 16-8) appear to be a particularly stable or unstable configuration? Explain.
