(Solved): Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, cou ...

Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a fourmembered, five-membered, or six-membered ring. To determine which ring is formed, ribose is treated with methanol in the presence of an acid catalyst. The products are then isolated and treated with \( \mathrm{NaIO}_{4} \) then with \( \mathrm{H}_{3} \mathrm{O}^{+} \). \( A \& B \) \( \frac{\text { 1. } \mathrm{NaIO}_{4}}{\text { 2. } \mathrm{H}_{3} \mathrm{O}^{+}} \rightarrow \mathrm{MeOH}+ \) products isomeric cyclic acetals with Ribose, \( \mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}_{5} \) formula \( \mathrm{C}_{6} \mathrm{H}_{12} \mathrm{O}_{5} \) Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of the sodium periodate digestion products. - Use the wedge/hash bond tools to indicate stereochemistry where it exists. - Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.