Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 25.SE, Problem 27VC
Interpretation Introduction
a)
Interpretation:
Identification of the configuration of sugars.
Interpretation Introduction
b)
Interpretation:
Identification of the configuration of sugars.
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(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 B
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.
a) Which of the following monosaccharides will react with Tollens' reagent? Circle all that
аpply.
СООН
CH2OH
CH2OH
OCH3
но-
H-
ОН
HO FH
OH
CH2OH
CH2OH
OH
II
III
IV
V
b) Decide whether the disaccharide shown below is a reducing or non-reducing sugar
CH2OH
но
Но-
ОН
CH2
но
Но
OH
OH
우 오
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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- 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 ОНarrow_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_forwardIdentify the reducing and non reducing sugars in the following. Which compounds, is any, will react with Tollen’s reagent?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_forward18-82 Identify each of the following Haworth projection formulas as an a-D-monosaccharide or a B-D-monosaccharide. ÇH,OH b. ÇH;OH a. OH Но OH ÓH ÓH ÓH с. CH,OH d. HOCH2 CH;OH OH HỎ OH OH ÓH ÓH 18-83 Draw tharrow_forwardDraw the Fischer projections of the four aldotetroses. Draw the D-sugar on the left and its L-isomer directly to the right of it. Be sure you select the appropriate hydroxy group so that the bond carbon is connected to the oxygen bond. Draw D sugar 1 Draw L sugar 1 Answer Bank ČH2OH CH2OH H -OH НО- Draw D sugar 2 Draw L sugar 2 CH2OH CH2OH 00 00 00 00arrow_forward
- Draw the product of the mutarotation of the monosaccharide shown below. ОН CH₂OH ОН ОН H3O+ ОН of вarrow_forwardОН 2. the Fischer projection that corresponds to the monosaccharide shown in the box. О н HO OH но- OH НО 0 OH OH OH H-OH -ОН 3. the Haworth projection that corresponds to the structure shown in the box. OCH, НО OH athul algasida О Н H-OH H-OH но-н но- HO -O OCH, OH O H H-OH НО-Н H-OH H-OH OH ОН НО НО OOCH, HO H-OH но-н но-н OH H-OH OH НО OH OCH, OH OH О н H-OH H-OH H НО но-н ОН НО -oOCH, ОН он онarrow_forwardBe sure to answer all parts. [1] classify the compound as a D or L monosaccharide; [2] draw the the enantiomer of the compound. H. но- H. -OH но- -H ČH,OH [1] (select) (select) L Darrow_forward
- 2. Provide a general name for the sugars and say whether they are D or L sugars. Draw the mirror image of each isomer. Fischer projection CH₂OH C=O HO -H H- OH H- -ОН CH₂OH Classification: Other isomer Fischer projection CHO HOH H- -OH H-OH HOH CH₂OH Classification: Classification: Other isomer Classification:arrow_forwardDraw the Fischer projection of each pair of compound. Identify the term that best describes both compounds using any of the following choices namely: Aldoses, ketoses, trioses, or aldohexoses.arrow_forwardDraw Haworth projection formulas for the a-anomer of monosaccharides with each of the following Fischer projection formulas. a. CHO HOH H- HO- H -ОН -Η OH CH₂OH b. CHO H -OH H -ОН HO H CH₂OHarrow_forward
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