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Dolbier HW Solutions 597 - 691 PHENOLS The more volatile...

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The more volatile compound (compound A), isolated by steam distillation, is the 2-nitro derivative. Intramolecular hydrogen bonding is possible between the nitro group and the hydroxyl group. The 4-nitro derivative participates in intermolecular hydrogen bonds and has a much higher boiling point; it is compound B. 24.21 The relationship between the target molecule and the starting materials tells us that two processes are required, formation of a diaryl ether linkage and nitration of an aromatic ring. The proper order of carrying out these two separate processes is what needs to be considered. The critical step is ether formation, a step that is feasible for the reactants shown: The reason this reaction is suitable is that it involves nucleophilic aromatic substitution by the addition elimination mechanism on a p -nitro-substituted aryl halide. Indeed, this reaction has been
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