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 MEOH 1. NalO4 A & B MEOH + products HO H* 2. H3O* isomeric cyclic acetals with formula CH12O5 он Он Ribose, CsH1005 Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of compounds A and B.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter20: Carbohydrates
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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 H30*.
OH
Меон
1. NalO4
2. H30*
A & B
MEOH + products
HO
H.
H*
isomeric cyclic
acetals with
formula CgH1205
ÕH
ÕH
Ribose, C5H1005
Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of compounds A and B.
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 H30*. OH Меон 1. NalO4 2. H30* A & B MEOH + products HO H. H* isomeric cyclic acetals with formula CgH1205 ÕH ÕH Ribose, C5H1005 Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of compounds A and B.
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