On treatment with phenylhydrazine, aldohexoses A and B give the same osazone. On

Chapter 0, Problem 23-38

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On treatment with phenylhydrazine, aldohexoses A and B give the same osazone. On treatment with warm nitric acid, A gives an optically inactive aldaric acid, but sugar B gives an optically active aldaric acid. Sugars A and B are both degraded to aldopentose C, which gives an optically active aldaric acid on treatment with nitric acid. Aldopentose C is degraded to aldotetrose D, which gives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D is degraded to Deduce the structures of sugars A, B, C, and D, and use Figure 23-3 to determine the correct names of these sugars.

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