Exam 16: Aromatic Compounds

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When cyclohexene is treated with KMnO4, H2O, the syn-1,2-diol is produced. What reaction occurs when benzene is similarly treated?

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How many distinct trichlorobenzene isomers are possible?

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Provide the structure of o-chlorotoluene.

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Is the [10]annulene shown below aromatic? Explain. Is the [10]annulene shown below aromatic? Explain.

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Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network. Classify the compound below as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

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The IR spectrum of m-xylene contains stretches which are characteristic of most aromatic hydrocarbons. List the peaks (in cm-1) associated with the aromatic C-C stretch and the aromatic C­H stretch.

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Provide the name of the compound shown below. Provide the name of the compound shown below.

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Which of the following structures is aromatic?

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Provide the structure of the major organic product which results when phenanthrene is treated with Br2 in carbon tetrachloride.

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In the UV-visible spectra of the following compounds, in which does lambda max appear at the highest wavelength?

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Why would the reaction below proceed at an extremely slow rate if at all? Why would the reaction below proceed at an extremely slow rate if at all?

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Is the molecule below aromatic, antiaromatic, or nonaromatic? Is the molecule below aromatic, antiaromatic, or nonaromatic?

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Provide an acceptable name for the compound below. Provide an acceptable name for the compound below.

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Classify 1,3,5-heptatriene as aromatic, antiaromatic, or nonaromatic. Assume planarity of the π network.

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Correctly name the following compound. Correctly name the following compound.

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Is the molecule below aromatic, antiaromatic, or nonaromatic? Is the molecule below aromatic, antiaromatic, or nonaromatic?

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Describe the benzenoid band which appears in the UV-visible spectrum of most aromatic hydrocarbons.

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Provide the structure of m-iodobenzoic acid.

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How many peaks are in the proton spin decoupled 13C NMR spectrum of the compound shown? How many peaks are in the proton spin decoupled <sup>13</sup>C NMR spectrum of the compound shown?

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Is the molecule below aromatic, antiaromatic, or nonaromatic? Is the molecule below aromatic, antiaromatic, or nonaromatic?

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