Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 15.4, Problem 7P
Interpretation Introduction
Interpretation:
Cyclooctatetraene reacts with potassium metal to form the stable cyclooctatetraene dianion, C6H82-. Whether the reaction will take place readily or not is to be stated. The geometry expected for the cyclooctatetraene dianion is also to be given.
Concept introduction:
According to Huckel’s Rule a planar, cyclic conjugated system will be
If the product is more stable than the reactant the reaction will proceed readily.
A planar geometry is expected for ions that are aromatic.
To state:
Whether the reaction in which cyclooctatetraene reacts with potassium metal to form the stable cyclooctatetraene dianion, C6H82- will take place readily or not.
To give:
The geometry expected for the cyclooctatetraene dianion.
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Cyclooctatetraene readily reacts with potassium metal to form the stablecyclooctatetraene dianion, C8H82- . Why do you suppose this reaction occurs so easily? What geometry do you expect for the cyclooctatetraene dianion?
Cyclooctatetraene readily reacts with potassium metal to form the stable cyclooctatetraene dianion, C8H82-. Why do you suppose this reaction occurs so easily? What geometry do you expect for the cyclooctatetraene dianion?
Measure the C-C-C and C-C-H bond angles in the energy-minimized model of cyclohexene and compare them with those predicted by VSEPR. Explain any differences.
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Give IUPAC names for the following compounds:Ch. 15.1 - Prob. 3PCh. 15.2 - Pyridine is a flat, hexagonal molecule with bond...Ch. 15.3 - Prob. 5PCh. 15.4 - Draw the five resonance structures of the...Ch. 15.4 - Prob. 7PCh. 15.4 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Prob. 10P
Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
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