Exam 14: Aromatic Compounds

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In which case is the indicated unshared pair of electrons NOT a contributor to the π\pi aromatic system?  In which case is the indicated unshared pair of electrons NOT a contributor to the   \pi  aromatic system?

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How many resonances would be expected in the broad-band decoupled C-13 spectra of: How many resonances would be expected in the broad-band decoupled C-13 spectra of:

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Which of the following substances,C8H9Cl,would exhibit five signals in its 13C NMR spectrum? Which of the following substances,C<sub>8</sub>H<sub>9</sub>Cl,would exhibit five signals in its <sup>13</sup>C NMR spectrum?

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Which of these would you expect to have significant resonance stabilization energy? Which of these would you expect to have significant resonance stabilization energy?

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Which of these is the single best representation for naphthalene? Which of these is the single best representation for naphthalene?

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On the basis of molecular orbital theory and Hückel's rule,which of these compounds should be aromatic? On the basis of molecular orbital theory and Hückel's rule,which of these compounds should be aromatic?    On the basis of molecular orbital theory and Hückel's rule,which of these compounds should be aromatic?

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In the molecular orbital model of cyclobutadiene,how many pairs of degenerate π\pi -molecular orbitals are there?

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Which of the following substances,formula C8H9Br,might exhibit the following 1H NMR spectrum ? singlet, δ\delta 2.45 Singlet, δ\delta 2.5 Multiplet, δ\delta 7.35  Which of the following substances,formula C<sub>8</sub>H<sub>9</sub>Br,might exhibit the following <sup>1</sup>H NMR spectrum ?  singlet, \delta 2.45 Singlet, \delta 2.5 Multiplet, \delta  7.35

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In which case is the indicated unshared pair of electrons NOT a contributor to the π\pi aromatic system?  In which case is the indicated unshared pair of electrons NOT a contributor to the   \pi  aromatic system?      In which case is the indicated unshared pair of electrons NOT a contributor to the   \pi  aromatic system?

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Of the following C-10 compounds,which is expected to possess the greatest resonance (delocalization)energy? Of the following C-10 compounds,which is expected to possess the greatest resonance (delocalization)energy?

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On the basis of molecular orbital theory and Hückel's rule,which molecules and/or ions should be non-aromatic? On the basis of molecular orbital theory and Hückel's rule,which molecules and/or ions should be non-aromatic?

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A compound that reacts like an alkane,alkene,alkyne,or one of their derivatives,is called an _____________ compound,while one that reacts like benzene is called an _____________ compound.

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Which dihydroxybenzene can yield only one mononitro derivative?

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Toluene is the name commonly assigned to:

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Humans do not have the biochemical ability to synthesize the benzene ring.Therefore,two amino acids,_____________ and ___________,are essential to the human diet.

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Which reagent(s)/technique would serve to distinguish between azulene and bicyclo[5.3.0]decane? Which reagent(s)/technique would serve to distinguish between azulene and bicyclo[5.3.0]decane?

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Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer. Briefly explain why the aromatic hydrocarbon shown possesses a significant dipole moment.Use diagrams as needed to illustrate/clarify your answer.

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Which of the following would you expect to be antiaromatic? Which of the following would you expect to be antiaromatic?

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In the molecular orbital model of benzene,how many pairs of degenerate π\pi -molecular orbitals are there?

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Which of the following would you expect to be aromatic? Which of the following would you expect to be aromatic?

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