Compound I (C11H14O2) is insoluble in water, aqueous acid,

Chapter 21, Problem 21.26

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Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3 but dissolves readily in 10% Na2CO3 and 10% NaOH. When these alkaline solutions are acidified with 10% HCl, compound I is recovered unchanged. Given this information and its 1 H-NMR spectrum, deduce the structure of compound I. 10 9 8 7 6 5 4 3 2 1 0 ppm Chemical Shift () C11H14O2 Compound I

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