Explain monosubstituted benzene ring

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Two isomeric compounds, A and B, are known to each have a monosubstituted benzene ring. Both have the formula C9H10O2 and both are insoluble in water. However, A dissolves in dilute aqueous NaOH, but B does not. A has an intense, broad IR absorption at 3000-2500 cm-1; this absorption is absent in the IR spectrum of B. Both A and B have strong IR absorptions in the region 1750-1650 cm-1. Give structures for A and B consistent with this information. Explain your reasoning. Is the information provided sufficient to uniquely define the structures A and B?

Reference no: EM13325577

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