An Optically Active D-Aldopentose Produced an Optically Inactive Alditol Upon

question 29

Essay

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

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