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

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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 (+)-glyceraldehyde. 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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Organic Chemistry

ISBN: 978-0321768414

8th edition

Authors: L. G. Wade Jr.

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