Exam 18: Reactions of Benzene and Substituted Benzenes

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What is the principle of microscopic reversibility?

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Propose a synthesis of the following compound benzene. Propose a synthesis of the following compound benzene.

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Provide the major resonance structures of the intermediate sigma complex in the reaction of benzene with the generic electrophile E+.

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List the following compounds in order of decreasing reactivity toward electrophilic aromatic substitution: toluene,benzene,fluorobenzene,nitrobenzene,phenol.

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Can one distinguish among the three isomeric xylenes using 13C NMR? Explain.

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Which of the following structures is the most important contributor to the resonance hybrid formed when toluene undergoes para nitration? Which of the following structures is the most important contributor to the resonance hybrid formed when toluene undergoes para nitration?

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What is the major product of the following reaction? What is the major product of the following reaction?

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Provide the major organic product of the following. Provide the major organic product of the following.

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