Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 40AP
Interpretation Introduction
Interpretation:
To draw the three-dimensional furanose form of ascorbic acid.
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Students have asked these similar questions
1. Draw Haworth projections of B-D-arabinofuranose and a-L-mannopyranose.
2. Consider the structure of the disaccharide drawn at right:
НО
`CH2
В
ОН
(a) Give the names and D/L designation for the two
monosaccharides linked together.
H,C-O
OHO
„OH OH
А:
НО
НО
A
В:
ОН
(b) In the structure, circle the anomeric carbon of each saccharide.
(c) Is each saccharide present in its a or ß anomer? Specify both A and B
(d) Would this disaccharide undergo mutarotation? Why or why not?
(e) Would this disaccharide react with Tollens and/or Benedicts reagent? Why or why
not?
(f) There are two reasons this is very unlikely to be a naturally occurring disaccharide.
What about its structure suggests this is true? Give both reasons.
Draw the Haworth projection for B-D-xylose
The Products of the reaction of L-glucose with the following
L-glucose [1] NH2NH4
[2] Ac2O,NaOAc
[3] N2OCH3
Products of the reaction of D-threose with the following
D-threose [1]NACN, HCI
[2] H2, Pd-Baso,
[3] H3O*
Classify the following monosaccharides as an aldose or ketose. I need help on number 5, a-d.
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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- Using Fischer projection structure where no cyclization took place, what product/s formed when D-galactose reacts with the following: CN- , H+ ; H2O (hydrolysis); NaBH4 NaBH4 CH3OH, HCl Acetic anhydridearrow_forwardWhat is the difference between1) an aldose and a ketose ?2) a pentose and a hexose ?3) D- and L-forms of sugars (in Fischer projection)?4) a furanose and a pyranose ? 5) α and ß-forms of sugars (in Haworth projection)?arrow_forwardRaffinose is a trisaccharide (C18H32O16) isolated from cottonseed meal. Raffinose doesnot reduce Tollens reagent, and it does not mutarotate. Complete hydrolysis of raffinosegives d-glucose, d-fructose, and d-galactose. When raffinose is treated with invertase,the products are d-fructose and a reducing disaccharide called melibiose. Raffinose isunaffected by treatment with a b@galactosidase, but an a@galactosidase hydrolyzes itto d-galactose and sucrose. When raffinose is treated with dimethyl sulfate and basefollowed by hydrolysis, the products are 2,3,4-tri-O-methylglucose, 1,3,4,6-tetraO-methylfructose, and 2,3,4,6-tetra-O-methylgalactose. Determine the completestructures of raffinose and melibiose, and give a systematic name for melibiose.arrow_forward
- (d) Draw the structure of the expected product when monosaccharide B undergo mutarotation upon dissolving in water in the presence of Tollens reagent (AGNO3, NHẠOH). он OH O. OH OH OH monosaccharide Barrow_forwardClassify each of the following monosaccharides as aldose or ketosearrow_forwardDraw the structure of: (a) a polysaccharide formed by joining D-mannose units in 1->4-ß-glycosidic linkages; (b) a polysaccharide formed by joining D-glucose units in 1->6-a-glycosidic linkages. The polysaccharide in (b) is dextran, a component of dental plaque.arrow_forward
- classify the following monosaccharides as aldoses/ketoses, triose/tetrose/pentose/hexose/ L/D enantiomer, and a-/Banomer when applicable.arrow_forwardGive Detailed explanation Solutionarrow_forward(A) Is the trisaccharide a reducing sugar? (B) Identify the type of glycosidic linkage of the colored bond.arrow_forward
- m) Which pyranose ring (A, B, C, or D) in the tetrasaccharide below is derived from D-altrose? The Fischer projections for the four aldohexoses that make up this tetrasaccharide are shown below. B C D HOH CHO CHO CHO CHO HO+H HTOH Fонно н HOH HOH H-OH H-OH H-+-OH H-TOHHOH HOH H+OH HOHнтон нон CHOH CHOH CHOH CHOH De D-glue Dalose Datrone i NH Į HOH STEP 1 OH, HO- answer 1. Just add arrows and charges for steps 1, 2, and 3 in formation of this enamine з no arrows needed here OH н Н ЮН -OH STEP 3 :ÖH н H STEP 2 на это про за почarrow_forward26. This compound is L-glyceraldehyde. Draw a stereochemically correct representation of C-1 and C-2 of D-glucose. CHO | HO—C—H | CH2OH 27. Categorize each of the following as an aldose, a ketose, or neither. 28. Define each in 20 words or less: (a) anomeric carbon; (b) enantiomers; (c) furanose and pyranose; (d) glycoside; (e) aldose and ketose. 29. A) Draw the structure of any aldohexose in the pyranose ring form. B) Draw the structure of the anomer of the aldohexose you drew above. C) How many asymmetric carbons (chiral centers) does each of these structures have? D) How many stereoisomers of the aldohexoses you drew are theoretically possible? 30. A) Define "reducing sugar." (b) Sucrose is a disaccharide composed of glucose and fructose (Glc(1 → 2)Fru). Explain why sucrose is not a reducing sugar, even though both glucose and fructose are.arrow_forwarda) Which of the following polysaccharides is a segment of amylose? CH2OH CH2OH CH2OH CH2OH OH OH OH OH ОН H H H OH OH OH ОН Structure I CH2OH CH2OH CH2OH CH2OH OH ОН OH ОН OH OH ОН OH Structure II b) Which one is a segment of cellulose? CH2OH CH2OH CH2OH CH2OH ОН OH OH ОН ОН OH ОН ОН ОН Structure I CH2OH CH2OH CH2OH CH2OH O. ОН ОН OH ОН OH OH OH OH Structure IIarrow_forward
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