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 boilingpoint; it is compound B.24.21The relationship between the target molecule and the starting materials tells us that two processesare required, formation of a diaryl ether linkage and nitration of an aromatic ring. The proper orderof 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 theaddition–elimination mechanism on ap-nitro-substituted aryl halide. Indeed, this reaction has been
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This note was uploaded on 10/03/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.