Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Question
Chapter 28, Problem 28.44P
Interpretation Introduction
(a)
Interpretation:
The relationship between A and B is to be predicted.
Concept introduction:
The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose. The anomers are cyclic monosaccharides, which differ in configuration at one stereogenic centre. These carbon atoms are called anomeric centre.
Interpretation Introduction
(b)
Interpretation:
The acyclic form of both A and B are to be drawn and each compound is to be named.
Concept introduction:
The structural representation of sugar molecule in cyclic form is known as Haworth projection. Sugar molecule that has six-membered-ring is known as pyranose and sugar molecule that has five-membered-ring is called furanose. The anomers are cyclic monosaccharides, which differ in configuration at one stereogenic centre. These carbon atoms are called anomeric centre.
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Students have asked these similar questions
For the following trisaccharide: a. Identify its monosaccharide units, specifying the anomeric forms of of each unit present on the trisaccharide. b. What are the glycosidic bonds present on the trisaccharide? c. Is the trisaccharide a reducing sugar?
A structural formula of a monosaccharide is shown below:
HOH₂C-
HO
OH
of
H
HO
OH
a. Classify this monosaccharide (e.g., ketotetrose)
b. Does it have the D or L configuration?
c. Specify the type of ring this structure has.
d. Is the configuration of the anomeric carbon alpha or beta?[
Consider the structure below:
HOH
H.
но
H.
H-
H.
он
он
он
HO.
H.
H.
OH O
H.
HO
он
H-
H.
он
H.
Is the trisaccharide a reducing sugar?
[ Choose ]
Identify the type of glycosidic linkage of the
[Choose ]
colored bond.
Chapter 28 Solutions
Organic Chemistry
Ch. 28 - Prob. 28.1PCh. 28 - Prob. 28.2PCh. 28 - Label each stereogenic center as R or S. a. b. c....Ch. 28 - Convert the ball-and-stick model to a Fischer...Ch. 28 - Prob. 28.5PCh. 28 - Prob. 28.6PCh. 28 - Prob. 28.7PCh. 28 - Prob. 28.8PCh. 28 - Prob. 28.9PCh. 28 - Prob. 28.10P
Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.23PCh. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35
Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - Convert each compound to a Fischer projection and...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - Prob. 28.43PCh. 28 - Prob. 28.44PCh. 28 - Prob. 28.45PCh. 28 - Draw both pyranose anomers of each aldohexose...Ch. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - Prob. 28.50PCh. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - What products are formed when each compound is...Ch. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - Prob. 28.58PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - Prob. 28.71PCh. 28 - Prob. 28.72PCh. 28 - Prob. 28.73PCh. 28 - Prob. 28.74PCh. 28 - Prob. 28.75PCh. 28 - Prob. 28.76PCh. 28 - Prob. 28.77PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.79P
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- a. Classify this monosaccharide (e.g., aldotriose)b. Does it have the D or L configuration? c. Which carbon and oxygen become bonded in the furanose ring form of this monosaccharide (e.g., C2O6, where O6 means the oxygen on carbon 6, or "not formed")? d. Which carbon and oxygen become bonded in the pyranose ring form of this monosaccharide e.g., C2O6 or "not formed"?arrow_forwardCompare the following monosaccharides and choose the best description. a. same sugar b. enantiomers c. diastereomers d. different sugarsarrow_forwardB4. CH₂OH H H но. H CH₂OH OH H AR Zeval O OH H H HO H O H OH OH H OH H OH H OH OH/ H H Lactose H OH НО. H OH H H Sucrose The structures of the disaccharides lactose and sucrose are shown above. a) Identify the monosaccharide residue that is common to both disaccharides. OH b) Identify and explain the diastereomeric relationship between two of the monosaccharide units in these sugars. c) Draw a simple mechanism for the lactase-catalyzed cleavage of the glycosidic bond in lactose. d) Explain why lactose and sucrose give different results in the Benedict's test.arrow_forward
- Draw a monosaccharide described in the following statements: 1.. The enantiomer of D-arabinose. 2. The enantiomer of D-ribulose. 3. A diastereomer of D-mannose in the D-configuration.arrow_forward9. A trisaccharide obtained from the partial hydrolysis of amylopectin showed two glycosidic linkages. A. Draw the structure of the trisaccharide B. If the trisaccharide is to be exhaustively methylated and subsequently hydrolyzed with an acid, how many different methylated products will be obtained? Draw their structures. C. Can an aqueous solution of the trisaccharide precipitate Cu as Cu₂O? If it can, encircle the potential carbonyl carbon(s) in the trisaccharide. D. Can the trisaccharide exist in different anomeric forms? If yes, draw their structures.arrow_forwardA glycosidic bond connects two monosaccharides to create sucrose (more commonly known as table sugar). Identify the type of glycosidic bond connecting the monosaccharides together as well as these two monosaccharides that are found in sucrose. a. α,ß-1,2-glycosidic bond, ß-L-glucose, and α- L-fructose b. α,ß-1,2-glycosidic bond, α-D-galactose, and ß-D-glucose c. α-1,4-glycosidic bond, α-D-glucose, and ß-D-fructose d. α,ß-1,2-glycosidic bond, α-D-glucose, and ß-D-fructosearrow_forward
- 1. Draw the two possible Haworth structures (both alpha and beta anomers) for the following monosaccharides and give their corresponding systematic names. [Show the stepwise process] A. D-Galactosearrow_forwardIn addition to have polyalcohol groups, what functional group(s) do monosaccharides have? O a. aldehyde group O b. both ketone and aldehyde groups O C. ether group O d. either ketone or aldehyde group e. ketone group Jump to... You are logged in as Alanie Fontenot (Log out) CHEM 1001/LEC/001X-2021/SPRING/SEMarrow_forwardWhich of the following types of monosaccharides have cyclic forms that involve a 5-membered ring? a. Aldohexoses and ketopentoses b. Aldopentoses and ketopentoses c. Aldopentoses and ketohexoses d. All of the above.arrow_forward
- Consider the tetrasaccharide stachyose drawn below. Stachyose is found in white jasmine, soybeans, and lentils. Because humans cannot digest it, its consumption causes flatulence.a. Label all glycoside bonds.b. Classify each glycosidic linkage as α or β and use numbers to designate its location between two rings (e.g., 1→4-β).c. What products are formed when stachyose is hydrolyzed with H3O+?d. Is stachyose a reducing sugar?e. What product is formed when stachyose is treated with excess CH3I, Ag2O?f. What products are formed when the product in (e) is treated with H3O+?arrow_forwardDraw a diastereomers of D- Glucosearrow_forwardi need an answer pleaseeeearrow_forward
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