An Optically Active D-Aldopentose Produced an Optically Inactive Aldaric Acid

question 42

Essay

An optically active D-aldopentose produced an optically inactive aldaric acid upon treatment with HNO₃. When this aldopentose was subjected to a Ruff degradation, a D-aldopentose was generated. This aldotetrose gave an optically inactive alditol upon reduction with NaBH₄. Use these data to provide the structure of the starting D-aldopentose.

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