A D-aldotetrose on oxidation with concentrated HNO3 resulted in optically inactive dicarboxylic acid. The structure of the D-aldotetrose is:
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Answer
(3) [figure]
Solution
An aldotetrose has two chiral carbons (C-2 and C-3). Conc. HNO3 oxidises both –CHO and –CH2OH to –COOH ⇒ 2,3-dihydroxybutanedioic acid (tartaric acid).
It is optically inactive only in the meso form, which has a plane of symmetry ⇒ both –OH on the same side of the Fischer projection.
D-sugar ⇒ –OH on C-3 (the carbon next to –CH2OH) on the right ⇒ –OH on C-2 also on the right ⇒ D-erythrose.
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∴ Option (3). (Option (4) is D-threose, which gives optically active tartaric acid; (1) and (2) are L-sugars.)
Answer: (3)