(Solution) - Arbutin a compound that can be isolated from the leaves -(2025 Original AI-Free Solution)

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Arbutin, a compound that can be isolated from the leaves of barberry, cranberry, and pear trees, has the molecular formula C12H16O7. When arbutin is treated with aqueous acid or with a ?-glucosidase, the reaction produces D-glucose and a compound X with the molecular formula C6H6O2. The 1H NMR spectrum of compound X consists of two singlets, one at ? 6.8 (4H) and one at ? 7.9 (2H). Methylation of arbutin followed by acidic hydrolysis yields 2, 3, 4, 6-tetra-O-methyl-d-glucose and a compound Y (C7H8O2). Compound Y is soluble in dilute aqueous NaOH but is insoluble in aqueous NaHCO3. The 1H NMR spectrum of Y shows a singlet at ? 3.9 (3H), a singlet at ? 4.8 (1H), and a multiplet (that resembles a singlet) at ? 6.8 (4H). Treating compound Y with aqueous NaOH and (CH3)2SO4 produces compound Z (C8H10O2). The 1H NMR spectrum of Z consists of two singlets, one at ? 3.75 (6H) and one at ? 6.8 (4H). Propose structures for arbutin and for compounds X, Y, and Z.