Solved: l-Gulose can be prepared from d-glucose by a route that begins with oxidation to

Chapter 25, Problem 25.47

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l-Gulose can be prepared from d-glucose by a route that begins with oxidation to d-glucaric acid, which cyclizes to form two six-membered-ring lactones. Separating the lactones and reducing them with sodium amalgam gives d-glucose and l-gulose. What are the structures of the two lactones, and which one is reduced to l-gulose?

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