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. When D-ribose is treated with methanol in the presence of an acid catalyst, two cyclic acetals, A and B, are formed, both with molecular formula C,H,0, These are separated, and each is treated with sodium periodate (Section 10.8C) followed by dilute aqueous acid. Both A and B yield the same three products in the same ratios. он о CHO СНО H+ CH,OH A +B ÕH 1. NalO, 2. H,0* НО CHO + CHOH + CH,OH ÕH CH,OH Isomeric cyclic acetals with molecular formula CH12O, D-Ribose (C;H1605) From this information, deduce whether the cyclic hemiacetal formed by D-ribose is four- membered, five-membered, or six-membered.
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. When D-ribose is treated with methanol in the presence of an acid catalyst, two cyclic acetals, A and B, are formed, both with molecular formula C,H,0, These are separated, and each is treated with sodium periodate (Section 10.8C) followed by dilute aqueous acid. Both A and B yield the same three products in the same ratios. он о CHO СНО H+ CH,OH A +B ÕH 1. NalO, 2. H,0* НО CHO + CHOH + CH,OH ÕH CH,OH Isomeric cyclic acetals with molecular formula CH12O, D-Ribose (C;H1605) From this information, deduce whether the cyclic hemiacetal formed by D-ribose is four- membered, five-membered, or six-membered.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.70P
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