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2. I he compound below known as salicin is an old natural painkiller (from tree bark). In the presence of water and acid, salicin will be metabolized into a cyclic hemiacetal and the actual drug. Please provide the products of this reaction and a detailed mechanism, using curved arrows to indicate the movement of electrons. Hint: The ether oxygen on the benzene ring is somewhat more basic than the other ether oxygen. ?? ?? cat. H+ and H2O ?? ?? ?? 3. (a) Shown below is the interconversion of two cyclic isomers of the sugar deoxyribose (of DNA fame). Provide a step-by-step mechanism for this reaction. Do not skip steps. ?? ?? ?? a-deoxy ribose H B-deoxy- H ribose HO H HO H (b) Predict the product of treatment of a-deoxyribose with ethanol in the presence of H

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ho ③(a) Otr 나 tbou 男G 115 U-

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