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Chemistry
10th Edition
ISBN: 9781305957404
Author: Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher: Cengage Learning
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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.](https://content.bartleby.com/qna-images/question/c98ae158-a489-45ee-83ba-dc9910276a0e/cda40ce0-d33b-48ee-ab43-3047c13e5f43/l9qi1a_thumbnail.png)
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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- CH₂CH3 + HBrarrow_forwardThe carbohydrate shown is a (an): но OH OH Triose tetrose pentose hexose heptosearrow_forwardHow much lactic acid (C3H6O3) is produced when 225g glucose (C6H12O6) is used as a substrate in fermentation. Assuming that the sugar is completely fermented to lactic acid.arrow_forward
- Draw the cyclic forms of beta-1,3'-d-ditalosearrow_forward1) The starch in 25kg (~1 bushel) of corn is hydrolyzed and in the process 1.8kg of water (H2O) is consumed. How many moles of glucose (C6H12O6) would you expect to be produced? C6H12O6 -> 2 CO2 + 2 C2H5OH. 2) If the glucose from the above hydrolysis is fermented, how many moles of ethanol (C2H5OH) would result? How many grams? 3) If ethanol has a density of 0.789g/ml, what would the volume of the ethanol be in ml? What would the volume be in gallons (1gal = 3785ml)? 4) The above ethanol could be converted to Vodka by diluting to 50% ethanol (adding enough water to double the volume). What would the volume of the resulting Vodka be in ml? If the volume of a “shot” of Vodka is 30ml, how many shots of vodka could be produced from a bushel of corn?arrow_forwardRibose, 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.arrow_forward
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