A D-aldotetrose on oxidation with concentrate | vedclass

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(C) -aldotetrose has the general structure $CHO-(CHOH)_2-CH_2OH$.Upon oxidation with concentrated $HNO_3$, the terminal aldehyde $(-CHO)$ and primary

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(C) -aldotetrose has the general structure $CHO-(CHOH)_2-CH_2OH$.Upon oxidation with concentrated $HNO_3$, the terminal aldehyde $(-CHO)$ and primary alcohol $(-CH_2OH)$ groups are oxidized to carboxylic acid $(-COOH)$ groups, resulting in a tartaric acid derivative $(HOOC-(CHOH)_2-COOH)$.For this dicarboxylic acid to be optically inactive, it must contain a plane of symmetry, making it a meso compound.In the Fischer projection of the $D$-aldotetrose, the $D$-configuration implies that the hydroxyl group at the chiral carbon furthest from the aldehyde group (i.e.,$C-3$) is on the right side.For the resulting dicarboxylic acid to be meso, the hydroxyl groups must be on the same side (erythro configuration) so that a plane of symmetry exists.Therefore, the $D$-aldotetrose must have both hydroxyl groups on the right side, which corresponds to $D$-erythrose.

$A$ $D$-aldotetrose on oxidation with concentrated $HNO_3$ resulted in an optically inactive dicarboxylic acid. The structure of the $D$-aldotetrose is:

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