Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 25.SE, Problem 29VC
Interpretation Introduction
Interpretation:
The configuration of the sugar has to be identified.
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6 сH-он
(5
4
OH
1
2
ОН
3
OH
(c) Trace and identify the acetal in the above monosaccharide.
(d) Draw the hemiacetal that results from above acetal.
(e) Draw the open chain equivalent of the sugar in part (d).
Consider the structure of raffinose, a trisaccharide found
in sugar beets and a number of higher plants.
HO
CH,OH
Но-
OH
OCH,
Но
Но
OH
НОСН
Но
CH,OH
ÓH
raffinose
(a) Classify raffinose as a reducing or nonreducing sugar,
and tell how you know.
(b) Identify the glycoside linkages in raffinose, and clas-
sify each as either a or B.
(c) Name the monosaccharides formed when raffinose is
hydrolyzed in
aqueous
acid.
(d) What products are formed when raffinose is treated
with dimethyl sulfate in NaOH, and then with aqueous
acid and heat?
6 CH2OH
4
OH
2
ОН
3
OH
(d) Draw the hemiacetal that results from above acetal.
(e) Draw the open chain equivalent of the sugar in part (d).
(f) Classify the monosaccharide below as a D-sugar or an L-sugar.
H
ОН
O.
ОН
CH2OH
ОН
ОН
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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- Draw the Haworth or Chair Haworth structures of the following disaccharides: (a) α-D-glucopyranosyl-(1,4)-β, D-galactopyranose (b) β,D-galactopyranosyl-(1,4)-α-D-glucopyranose (c) β-D-glucopyranosyl-(1,4)-α,D-galactopyranose. Identify all anomeric carbons and hemiacetal, acetal, hemiketal, and ketal linkages.arrow_forward(a) Draw the more stable chair form of fucose, an essential monosaccharide needed in the diet and a component of carbohydrates on mammalian and plant cell surfaces. (b) Classify fucose as a D- or L-monosaccharide. (c) What two structural features are unusual in fucose?arrow_forwardm) 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_forward
- (g) Using appropriate prefixes/infixes/suffixes (ketohentese, aldahentase, etc.), classify each of the monosaccharides shown below. СНО CH2OH O: HOI но ОН OH HO H. CH2OH CH2OH I II (h) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. CH2OH CH2OH CH2OH CH2OH O. ОН OH OH OH OH OH ОН OH OH OH ОН OH OH OH OH OH I II III IV | (i) Identify B-D-altrose and oa-D-altrose from the monosaccharides shown below. VI I CH2OH CH2OH II V OH III ОН IV H OH Harrow_forwardI) Draw a proper Fischer projection for the following molecule. Assign each stereogenic carbon as either (R) or (S) and determine if the molecule is either a (D) or (L)-sugar, is this aldose or ketose? ОН он он ОНarrow_forwardArabinoxylan is a copolymer of arabinose and xylose-two five-carbon sugars. A portion of the polysaccharide is shown here. (a) Identify and classify each glycosidic linkage. (b) Based on the structure, do you think arabinoxylan functions as a storage polysaccharide or a structural polysaccharide? Explain your reasoning. HOH,C. OH Но OH OH но но OH Но LO. Но HOH,C HOH2C НО OH OH CH,OHarrow_forward
- (h) Identify B-D-altrose and a-D-altrose from the monosaccharides shown below. VI I CH2OH O. CH2OH II H V ОН, IV H III OH OH H (i) The monosaccharide below is a(n) (d-aldopentose, R-aldopentose, S- aldopentose, L-aldopentose, D-aldopentose).arrow_forwardRegarding 4-O- (α-D-psychofuranosyl) -β-D-allopyranose. Please indicate the RIGHT alternative: (a) The disaccharide reacts with CH3OH in an acid medium to form a glycoside that cannot be oxidized with HNO3. (b) It is a reducing disaccharide only in basic medium. (c) In the structure there is only one glycosidic bond that is of the type β 1-O-4 ' (d) The hydrolysis products of this disaccharide do not show mutarrotation. (e) The disaccharide structure contains two six-membered rings.arrow_forward(a) Convert each cyclic monosaccharide into a Fischer projection of its acyclic form. (b) Name each monosaccharide. (c) Label the anomer as α or β.arrow_forward
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