28. Carbohydrates
Monosaccharides - Drawing Fischer Projections
Problem 23
Textbook Question
Textbook QuestionThe relative configurations of the stereoisomers of tartaric acid were established by the following syntheses: (1) D-(+)-glyceraldehyde (with HCN) --> diastereomers A and B (separated) (2) Hydrolysis of A and B using aqueous Ba(OH)2 gave C and D, respectively. (3) HNO3 oxidation of C and D gave (-)-tartaric acid and meso-tartaric acid, respectively. (a) You know the absolute configuration of D-(+)-glyceraldehyde. Use Fischer projections to show the absolute configurations of products A, B, C, and D. (b) Show the absolute configurations of the three stereoisomers of tartaric acid: (+)-tartaric acid, (-)-tartaric acid, and meso-tartaric acid.
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