Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four- membered, 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 NaIO4 then with H3O+. OH HO OH OH Ribose, C5H10O5 H MeOH H* A & B isomeric cyclic acetals with formula C6H₁2O5 1. NalO4 2. H₂O* MeOH products 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.

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Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-
membered, 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 NaIO4 then with H3O+.
OH
HO
OH
OH
Ribose, C5H10O5
H
MeOH
H*
A & B
isomeric cyclic
acetals with
formula C6H₁2O5
1. NalO4
2. H₂O*
MeOH products
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.
Transcribed Image Text:Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four- membered, 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 NaIO4 then with H3O+. OH HO OH OH Ribose, C5H10O5 H MeOH H* A & B isomeric cyclic acetals with formula C6H₁2O5 1. NalO4 2. H₂O* MeOH products 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.
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