In 1891, Emil Fischer determined the structures of glucose and the seven other d-aldohexoses using only simple chemical reactions and clever reasoning about stereochemistry and symmetry. He received the Nobel Prize for this work in 1902. Fischer had determined that d-glucose is an aldohexose, and he used Ruff degradations to degrade it to (+)-glyceraldehyde. Therefore, the eight d-aldohexose structures shown in Figure 23-3 are the possible structures for glucose. Pretend that no names are shown in Figure 23-3 except for glyceraldehyde, and use the following results to prove which of these structures represent glucose, mannose, arabinose, and erythrose.
(b) Upon Ruff degradation, arabinose gives the aldotetrose erythrose. Nitric acid oxidation of erythrose gives an optically inactive aldaric acid, meso-tartaric acid. What is the structure of erythrose?
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