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

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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