Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 24P

(a) In 1960 T. Katz (Columbia University) showed that cyclooctatetraene adds two electrons when treated with potassium metal and forms a stable, planar dianion, C 8 H 8 2 (as the dipotassium salt):

Chapter 14, Problem 24P, 14.24	(a)	In 1960 T. Katz (Columbia University) showed that cyclooctatetraene adds two electrons , example  1

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 C 8 H 6 2 (as the dilithium salt).

Chapter 14, Problem 24P, 14.24	(a)	In 1960 T. Katz (Columbia University) showed that cyclooctatetraene adds two electrons , example  2

Propose a reasonable structure for the product and explain why it is stable.

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Cyanic acid (HOCN) and isocyanic acid (HNCO) dissolve in water to give the same anion upon deprotonation. (i) Draw Lewis structures for cyanic acid and isocyanic acid. (ii) Using arrow pushing and resonance, account for the fact that each acid gives the same anion on loss of H+ when reacted with NaOH.
(b) 3-methyl-2-butanol reacts with concentrated sulphuric acid to form 2-methyl-2- butene. Write the mechanism for the reaction.
(c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.

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