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a. Cyclooctatetraene (COT) is shown below. use the Hückel molecular orbital theory "polygon-in-circle," method to draw a diagram of the relative energies of the n molecular orbitals for COT (you should also fill out this diagram with the correct number of t electrons and indicate which molecular orbitals are bonding, nonbonding, and antibonding). Based solely on the MO diagram you may have learned in class), would this hypothetical planar COT be aromatic, anti-aromatic, or non-aromatic? Assume the molecule is planar, (do not consider anything else about the structure

a. Cyclooctatetraene (COT) is shown below. use the Hückel molecular orbital theory "polygon-in-circle," method to draw a diagram of the relative energies of the n molecular orbitals for COT (you should also fill out this diagram with the correct number of t electrons and indicate which molecular orbitals are bonding, nonbonding, and antibonding). Based solely on the MO diagram you may have learned in class), would this hypothetical planar COT be aromatic, anti-aromatic, or non-aromatic? Assume the molecule is planar, (do not consider anything else about the structure

Chemistry: Principles and Practice
Chemistry: Principles and Practice
3rd Edition
ISBN:9780534420123
Author:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Publisher:Daniel L. Reger, Scott R. Goode, David W. Ball, Edward Mercer
Chapter10: Molecular Structure And Bonding Theories
Section: Chapter Questions
Problem 10.101QE: The molecular orbital diagram of NO shown in Figure 10.47 also applies to OF. Draw the complete...
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Parts A,B, and C are all apart of this problem.
1. a. Cyclooctatetraene (COT) is shown below. use the Hückel molecular orbital theory "polygon-in-circle," method to draw a diagram of the relative energies of the t molecular orbitals for COT (you should also fill out this diagram with the correct number of t electrons and indicate which molecular orbitals are bonding, nonbonding, and antibonding). Based solely on the MO diagram (do not consider anything else about the structure you may have learned in class), would this hypothetical planar COT be aromatic, anti-aromatic, or non-aromatic? Assume the molecule is planar,
Transcribed Image Text:1. a. Cyclooctatetraene (COT) is shown below. use the Hückel molecular orbital theory "polygon-in-circle," method to draw a diagram of the relative energies of the t molecular orbitals for COT (you should also fill out this diagram with the correct number of t electrons and indicate which molecular orbitals are bonding, nonbonding, and antibonding). Based solely on the MO diagram (do not consider anything else about the structure you may have learned in class), would this hypothetical planar COT be aromatic, anti-aromatic, or non-aromatic? Assume the molecule is planar,
b. In nature, COT adopts a "tub-shape," as was shown in class. Assuming the molecule distorts to this non-planar geometry is COT aromatic, anti-aromatic, or non-aromatic? C. George Olah and coworkers reported a relative of COT shown above, 1,4- dimethylcyclooctatetraene dication. The 'H NMR shows a set of 3 signals with relative integrations of 2:1:3 at 9.96 (two overlapped peaks), 9.90, and 3.98 ppm chemical shift. Explain why the signals at 9.96 and 9.90 show such a low field chemical shift (hint: it is not alone sufficient to say this is due to the positive charge). Second hint: use the a MO diagram you created in part a. to help answer this.
Transcribed Image Text:b. In nature, COT adopts a "tub-shape," as was shown in class. Assuming the molecule distorts to this non-planar geometry is COT aromatic, anti-aromatic, or non-aromatic? C. George Olah and coworkers reported a relative of COT shown above, 1,4- dimethylcyclooctatetraene dication. The 'H NMR shows a set of 3 signals with relative integrations of 2:1:3 at 9.96 (two overlapped peaks), 9.90, and 3.98 ppm chemical shift. Explain why the signals at 9.96 and 9.90 show such a low field chemical shift (hint: it is not alone sufficient to say this is due to the positive charge). Second hint: use the a MO diagram you created in part a. to help answer this.
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