Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.SE, Problem 39AP
Interpretation Introduction
Interpretation:
To determine the configuration of ascorbic acid.
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The structure of 4 isomers of an aldotetrose carbohydrate are given.
1) select every structure that is a diastereomer of structure D
A, B, or C?
2) select every structure that is a enantiomer of structure C
D, B, or A?
3) select every structure that is a stereoisomer of structure D
A, B, or C
Monosaccharides can be drawn in a variety of ways, and in truth, often a mixture of cyclic compounds is present in a solution. Identify each monosaccharide, including its proper D,L designation, drawn in a less-than-typical fashion.
D
The following disaccharide contains a(n) (blank]-glycosidic linkage.
HO
CH₂OH
ОН
Oa-1,4
OB-1,4
a-1,6
O B-1,6
0
OH
Question 6
double bond
ssignments/syllabus
ester bond
ether bond
amide bond
HO
A glycosidic bond between two monosaccharides can also be classified as a(n) [blank).
OH
OH
Melebi
OH
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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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- Consider the following compound, which is used by insects and some fungi to store energy:arrow_forwarda) Which of the following monosaccharides will react with Tollens' reagent? Circle all that apply. СООН CH2OH CH2OH OCH3 но- H- O: OH но H- но—н OH ČH2OH ČH2OH ÓH II III IV V b) Which of the following carbohydrates is sucrose? OH OH OH но OH HO, O. OH "OH HO OH Он HO OH II I HO, HO. Он HO, HO. HO, OH Но Он но. OH HO,, HO, OH HOl HO OH но он III Он HO IV HO ноarrow_forwardIdentify the names of the monosaccharides in the picture and the type of glycosidic bond of the disaccharide in the picture.arrow_forward
- Please refer to the monosaccharides below when answering questions (a) – (). CHO CHO СНО СНО CHO НО H- HO Но- HO H- ОН но- H- ОН Но- H HO Но- H ОН Но H- H- ОН НО H- Но- H- ОН Но но- H- HO H- H- HO- CH2OH CH2OH ČH2OH CH2OH CH2OH I II III IV V (a) Draw the monosaccharide that results when III is treated with Br2/H2O. (b) Draw the monosaccharide that results when III is treated with 1. NaBH4/ 2. H2O. (c) Draw the monosaccharide that results when II is treated with the following reagents: 1. Br,/H20 2. Ca(ОН)2 3. H2O2/Fe3+arrow_forwardName the two monosaccharide units of which trehalose is composedarrow_forwardqarrow_forward
- (A) Is the trisaccharide a reducing sugar? (B) Identify the type of glycosidic linkage of the colored bond.arrow_forwardOH ОН Which monosaccharide has a greater heat of combustion, B-D-glucopyranose or B-D-allopyranose? Explain. но НО Но OH OH OH OH OH B-D-Glucopyranose B-D-Allopyranosearrow_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
- 1. Which of the following is not true to the monosaccharide below? H. ОН но- -H- но ОН ĆH2OH O It is the Fischer Projection of D-glucose. It is an aldohexose having 4 chiral centers and 24 stereoisomers. It is has a D-glucose because OH- group bonded to the highest numbered chiral C is pointing to the right. It is a polyhydroxy ketone having 8 enantiomeric pair.arrow_forward5. Cholesterol is one of the important component of animal cell membrane. Label circled chiral centers as R/S, and circle the rest of chiral centers in this compound. b a H НО Cholesterolarrow_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_forward
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