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Cyclooctatetraene (8-annulene) is non-aromatic because all four pi bonds are not found in the same plane in its lowest energy conformation. If this compound is reduced by two electrons to generate the dianion, it exhibits aromatic characteristics. Draw the pi MO diagram for these compounds if they are planar, and fill in the electrons. Based on that picture explain the difference in their aromaticity.

Cyclooctatetraene (8-annulene) is non-aromatic because all four pi bonds are not found in the same plane in its lowest energy conformation. If this compound is reduced by two electrons to generate the dianion, it exhibits aromatic characteristics. Draw the pi MO diagram for these compounds if they are planar, and fill in the electrons. Based on that picture explain the difference in their aromaticity.

Organic Chemistry
Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
Section16.SE: Something Extra
Problem 25VC: The following molecular model of a dimethyl-substituted biphenyl represents the lowest-energy...
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Cyclooctatetraene (8-annulene) is non-aromatic because all four pi bonds are not found in the same plane in its lowest energy conformation. If this compound is reduced by two electrons to generate the dianion, it exhibits aromatic characteristics. Draw the pi MO diagram for these compounds if they are planar, and fill in the electrons. Based on that picture explain the difference in their aromaticity.
Transcribed Image Text:Cyclooctatetraene (8-annulene) is non-aromatic because all four pi bonds are not found in the same plane in its lowest energy conformation. If this compound is reduced by two electrons to generate the dianion, it exhibits aromatic characteristics. Draw the pi MO diagram for these compounds if they are planar, and fill in the electrons. Based on that picture explain the difference in their aromaticity.
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