Concept explainers
(a)
Interpretation: The given compounds A, B and C are to be labeled as D or L-sugar.
Concept introduction: A sugar molecule in which hydroxyl group of second last carbon atom is on the left and right side of the horizontal line is known as
(b)
Interpretation: The relation between A and B, A and C, B and C is to be determined from enantiomers, diastereomers and constitutional isomers.
Concept introduction: Two compounds which are non-superimposable mirror images of each other are known as enantiomers. Whereas two compounds which are neither superimposable nor mirror images to each other are known as diastereomer. On the other hand, two compounds that have same molecular formula but different structural arrangement of atoms are known as constitutional isomers.
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ORGANIC CHEMISTRY (LOOSELEAF)
- (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(a) Convert each cyclic monosaccharide into a Fischer projection of its acyclic form. (b) Name each monosaccharide. (c) Label the anomer as a or ß.arrow_forward4 Draw a chair conformation for a β anomer of a disaccharide in which the two units of D-glucopyranose are joined by an α-1,6-glycosidic 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_forwardThe anticoagulant heparin is a polysaccharide that contains alternating residues of -D- glucuronic acid-6- sulfate and N-sulfo-D-glucosamine-6sulfate connected by (1 B 4)- glycosidic linkages. Draw a part of heparin that shows one each of the two residues.arrow_forward9 A disaccharide consists of the molecules of D-glucose and D-glucosamine joined by a (1a, 1b)-glucosidic bond. a) Draw the structure of the disaccharide (Haworth projection) if you know that in D- glucose the anomeric carbon has an a-configuration. b) Give the name of the union you drew in question a. c) Draw the structure of the product (cantilever conformation) resulting from the effect of excess acetic anhydride and pyridine on the disaccharide. Hint: D-glucosamine has the same structure as D-glucose, but C-2 has an amino group instead of a hydroxyl.arrow_forward
- Barrow_forward6 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_forward1. 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.arrow_forward
- Consider the following compound, which is used by insects and some fungi to store energy:arrow_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_forwardMonosaccharides 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.arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning