Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.6, Problem 21P
Interpretation Introduction
Interpretation:
The Kiliani–Fischer synthesis, is a method for synthesizing monosaccharides. It proceeds via synthesis and hydrolysis of a cyanohydrin, thus elongating the carbon chain of an aldose by one carbon atom while preserving stereochemistry on all the previously present chiral carbons.
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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.
Draw the products from Killiani-Fischer reaction of D-ribose and L-Xylose.
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Chapter 25 Solutions
Organic Chemistry
Ch. 25.1 - Prob. 1PCh. 25.2 - Prob. 2PCh. 25.2 - Prob. 3PCh. 25.2 - Prob. 4PCh. 25.2 - Prob. 5PCh. 25.3 - Prob. 6PCh. 25.3 - Prob. 7PCh. 25.4 - Prob. 8PCh. 25.4 - Prob. 9PCh. 25.4 - Prob. 10P
Ch. 25.5 - Prob. 11PCh. 25.5 - Prob. 12PCh. 25.5 - Prob. 13PCh. 25.5 - Prob. 14PCh. 25.5 - Prob. 15PCh. 25.6 - Prob. 16PCh. 25.6 - Prob. 17PCh. 25.6 - Prob. 18PCh. 25.6 - Prob. 19PCh. 25.6 - Prob. 20PCh. 25.6 - Prob. 21PCh. 25.6 - Prob. 22PCh. 25.6 - Prob. 23PCh. 25.7 - Prob. 24PCh. 25.8 - Show the product you would obtain from the...Ch. 25.SE - Prob. 26VCCh. 25.SE - Prob. 27VCCh. 25.SE - Prob. 28VCCh. 25.SE - Prob. 29VCCh. 25.SE - Prob. 30MPCh. 25.SE - Prob. 31MPCh. 25.SE - Glucosamine, one of the eight essential...Ch. 25.SE - D-Glicose reacts with acetone in the presence of...Ch. 25.SE - Prob. 34MPCh. 25.SE - Prob. 35MPCh. 25.SE - Prob. 36APCh. 25.SE - Prob. 37APCh. 25.SE - Prob. 38APCh. 25.SE - Prob. 39APCh. 25.SE - Prob. 40APCh. 25.SE - Assign R or S configuration to each chirality...Ch. 25.SE - Prob. 42APCh. 25.SE - Prob. 43APCh. 25.SE - Prob. 44APCh. 25.SE - Prob. 45APCh. 25.SE - Prob. 46APCh. 25.SE - Prob. 47APCh. 25.SE - Prob. 48APCh. 25.SE - Prob. 49APCh. 25.SE - Prob. 50APCh. 25.SE - Prob. 51APCh. 25.SE - Prob. 52APCh. 25.SE - Prob. 53APCh. 25.SE - Prob. 54APCh. 25.SE - Prob. 55APCh. 25.SE - Prob. 56APCh. 25.SE - Prob. 57APCh. 25.SE - Prob. 58APCh. 25.SE - Prob. 59APCh. 25.SE - Prob. 60APCh. 25.SE - Prob. 61APCh. 25.SE - Prob. 62APCh. 25.SE - Prob. 63APCh. 25.SE - D-Mannose reacts with acetone to give a...Ch. 25.SE - Prob. 65APCh. 25.SE - Prob. 66APCh. 25.SE - Prob. 67APCh. 25.SE - Prob. 68APCh. 25.SE - Prob. 69APCh. 25.SE - Prob. 70APCh. 25.SE - Prob. 71AP
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- Trehalose, C12H22O11, is a nonreducing sugar that is only 45% as sweet as sugar. When hydrolyzed by aqueous acid or the enzyme maltase, it forms only d-glucose. When it is treated with excess methyl iodide in the presence of Ag2O and then hydrolyzed with water under acidic conditions, only 2,3,4,6-tetra-O-methyl-d-glucose is formed. Draw the structure of trehalosearrow_forwardTreatment of either anomer of fructose with excess ethanol in the presence of a trace ofHCl gives a mixture of the a and b anomers of ethyl-d-fructofuranoside. Draw the startingmaterials, reagents, and products for this reaction. Circle the aglycone in each productarrow_forward4) Structure: the appropriate box. CHO -OH H- HO- -H HO -H Write the requested cyclized form of the given carbohydrates in B-pyranose a-furanose CH₂OHarrow_forward
- Trehalose, C12H22O11, is a nonreducing sugar that is only 45% as sweet as sugar. When hydrolyzed by aqueous acid or the enzyme maltase, it formsonly d-glucose. When it is treated with excess methyl iodide in the presence of Ag2O and then hydrolyzed with water under acidic conditions, only2,3,4,6-tetra-O-methyl-d-glucose is formed. Draw the structure of trehalose.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. 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 NaIO, then with H₂O*. HO OH OH OH Ribose, C5H10O5 H 9.81 ** MeOH H* A & B isomeric cyclic acetals with formula C6H12O5 Assuming that ribose formed a five-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. 1. NalO4, 2. H₂O* MeOH products 4 SIF Previous Nextarrow_forwardThe most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the a or ß anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_forward
- (a) Label compounds A, B, and C as D- or L-sugars. (b) How are compounds A and B related? A and C? B and C? Choose from enantiomers, diastereomers, or constitutional isomers.arrow_forwardDraw the products formed when ß-D-galactose is treated with each reagent.a. Ag2O + CH3Ib. NaH + C6H5CH2Clc. The product in (b), then H3O+d. Ac2O + pyridinee. C6H5COCl + pyridinef. The product in (c), then C6H5COCl + pyridinearrow_forwardWhich aldopentose gives the same aldaric acid as D-xylose? Which aldopentose gives the same aldaric acid as D-arabinose?arrow_forward
- Why is molecule "A" the major acetal formed when d-erythrose reacts with H2SO4 and acetone as opposed to molecule "B"?arrow_forwardThe structures of an aldose and a ketose are shown here. An aldose contains an aldehyde group. Click on that group.arrow_forwardDraw the products formed when α-D-galactose is treated with each reagent: i. CH3I (excess), Ag2O ii. CH3OH, H3O+ iii. NaOH, H2O iv. Br2, H2Oarrow_forward
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