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.

Chemistry

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ISBN:9781305957404

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Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

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Question

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.

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