Exam 15: Benzene and Aromaticity

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​Draw the different resonance forms of phenanthrene.

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Which of the choices arranges numbered protons in the following substance in order of increasing downfield chemical shift in a proton NMR? Atoms other than carbon and hydrogen are labeled. Which of the choices arranges numbered protons in the following substance in order of increasing downfield chemical shift in a proton NMR? Atoms other than carbon and hydrogen are labeled.

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Draw: p-chlorobenzaldehyde

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Exhibit 15-6 Consider the data below to answer the following question(s). C9H12;1H NMR: 6.65 δ (singlet,3H) 2.25 δ (singlet,9H) -Refer to Exhibit 15-6.Describe the signal at 6.65 δ in terms of its splitting,integration and chemical shift.

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Draw the resonance structures of cyclooctatetraene.

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Most alkyl halides are nonpolar covalent compounds and,therefore,are soluble in nonpolar solvents and insoluble in water.Cycloheptatrienyl bromide is an unusual alkyl halide in that it is insoluble in nonpolar solvents,but is readily soluble in water! This behavior is consistent with cycloheptatrienyl bromide being an ionic compound.Why does cycloheptatrienyl bromide exist as an ionic compound? Explain by comparing the covalent structure to the ionic structure. Most alkyl halides are nonpolar covalent compounds and,therefore,are soluble in nonpolar solvents and insoluble in water.Cycloheptatrienyl bromide is an unusual alkyl halide in that it is insoluble in nonpolar solvents,but is readily soluble in water! This behavior is consistent with cycloheptatrienyl bromide being an ionic compound.Why does cycloheptatrienyl bromide exist as an ionic compound? Explain by comparing the covalent structure to the ionic structure.

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Draw the MO energy diagram for the cycloheptatrienyl anion and classify the anion as aromatic or antiaromatic.

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