Concept explainers
(a) In 1960 T. Katz (Columbia University) showed that cyclooctatetraene adds two electrons when treated with potassium metal and forms a stable, planar dianion,
Use the molecular orbital diagram given in Fig. 14.7 and explain this result.
(b) In 1964 Katz also showed that removing two protons from the compound below (using butyllithium as the base) leads to the forma-tion of a stable dianion with the formula
Propose a reasonable structure for the product and explain why it is stable.
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Organic Chemistry
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