Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Textbook Question
Chapter 4, Problem 1LGP
The predominant conformation for D-glucose is shown here. Why is it not surprising that D-glucose is the most commonly found sugar in nature? (Hint: Look up structures for sugars such as D-galactose and D-mannose, and compare these with D-glucose.)
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Students have asked these similar questions
Glycosaminoglycans (GAGs) are heteropolysaccharides composed of repeating disaccharide units. These units have some
similar characteristics that allow them to be identified as GAGS.
Which of the structures are examples of glycosaminoglycans?
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Complete the following for each of the following structures below.
Determine whether it is an aldohexose, aldopentose, ketohexose or ketopentose.
Label the chiral carbon atoms using an asterisk.
Determine the number of stereoisomers it can have.
Label the molecule as a D or an L sugar.
*IMPORTANT NOTE: The most common ketoses have the ketone
function at carbon 2.
5. Circle the carbonyl group in the structures below and specify if the
structures correspond to an aldose or ketoses.
O
CH₂OH
C=O
CH₂OH
H
C
H-C-OH
CH₂OH
6. The sugar below is glucose. Number the carbons starting with the
carbonyl group. Determine how many carbons are chiral centers
(circle the chiral centers and list them in the space below).
H-C-OH
HO-C-H
H-C-OH
H-C-OH
CH₂OH
D-Glucose,
an aldohexose
H-C-OH
C-0
HO-C-H
H-C-OH
H-C-OH
CH₂OH
D-Fructose,
a ketohexose
Chiral centers:
7. Based on your answer above, calculate the number of possible
stereosiomers that glucose has. Remember, the equation to do that is
2" where n is the number of chiral centers and two is the number of
configurations (E.g. D and L are two configurations).
CHO
H-C-OH
Achiral centers:
8. The molecules below (fisher projections) correspond to
glyceraldehyde. Glyceraldehyde has two configurations D and L. The
configuration is determined…
Chapter 4 Solutions
Organic Chemistry
Ch. 4 - Prob. 1PPCh. 4 - Which structure does not represent...Ch. 4 - Prob. 3PPCh. 4 - Draw bond-line formulas for all of the isomers of...Ch. 4 - Prob. 5PPCh. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Draw bond-line formulas and give IUPAC...Ch. 4 - Practice Problem 4.8 Give names for the following...Ch. 4 - Prob. 9PPCh. 4 - Prob. 10PP
Ch. 4 - Prob. 11PPCh. 4 - Give the structures and IUPAC names for all the...Ch. 4 - Prob. 13PPCh. 4 - Practice Problem 4.14 Show by a calculation (using...Ch. 4 - Practice Problem 4.15 Write structures for the cis...Ch. 4 - Practice Problem 4.16
(a) Write structural...Ch. 4 - Practice Problem 4.17 Write a conformational...Ch. 4 - Practice Problem 4.18
(a) Write the two...Ch. 4 - Prob. 19PPCh. 4 - Practice Problem 4.20 (a) What is the index of...Ch. 4 - Practice Problem 4.21
Zingiberene, a fragrant...Ch. 4 - Practice Problem 4.22 Carbonyl groups also count...Ch. 4 - Prob. 23PCh. 4 - Give systematic IUPAC names for each of the...Ch. 4 - Prob. 25PCh. 4 - Write the structure and give the IUPAC systema.tic...Ch. 4 - 4.27. Write the structure(s) of the simplest...Ch. 4 - Prob. 28PCh. 4 - 4.29. Write structures for the following...Ch. 4 - Prob. 30PCh. 4 - A spiro ring junction is one where two rings that...Ch. 4 - 4.32. Tell what is meant by a homologous series...Ch. 4 - Four different cycloalkenes will all yield...Ch. 4 - 4.34. (a) Three different alkenes yield...Ch. 4 - Prob. 35PCh. 4 - Prob. 36PCh. 4 - 4.37. Write the structures of two chair...Ch. 4 - Prob. 38PCh. 4 - Without referring to tables, decide which member...Ch. 4 - Prob. 40PCh. 4 - 4.41. Which compound would you expect to be the...Ch. 4 - Prob. 42PCh. 4 - 4.43. Write the two chair conformations of each of...Ch. 4 - Provide an explanation for the surprising fact...Ch. 4 - Prob. 45PCh. 4 - 4.46. Specify the missing compounds and/or...Ch. 4 - Consider the cis and trans isomers of...Ch. 4 - Prob. 48PCh. 4 - Open the energy-minimized 3D Molecular Models on...Ch. 4 - 4.50. Open the 3D Molecular Models on the book’s...Ch. 4 - 4.51. Open the 3D Molecular Model on the book’s...Ch. 4 - 1. The predominant conformation for D-glucose is...Ch. 4 - Prob. 2LGPCh. 4 - When 1,2-dimethylcyclohexene is allowed to react...Ch. 4 - Prob. 4LGPCh. 4 - Prob. 1QCh. 4 - Select the correct name of the compound whose...Ch. 4 - Select the correct name of the compound whose...Ch. 4 - Prob. 4QCh. 4 - 4.5 How many isomers are possible for C3H7Br?
(a)...Ch. 4 - 4.6 Which isomer of 1,3-dimethylcyclohexane is...Ch. 4 - 4.7. Which is the lowest energy conformation of...Ch. 4 - Supply the missing structuresCh. 4 - Supply the missing reagents in the box:Ch. 4 - The most stable conformation of...
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- The disaccharide maltose is shown below. It contains an a-1,4'-glycosidic linkage between two sugars. Number the carbons on each using the correct numbering scheme for sugars (the sugar on the right should be numbered 1', 2', 3', etc.). Circle the glycosidic bond. Name the two monosaccharides that make up maltose. OH Sugar 1 (left): Sugar 2 (right): Type of glycosidic bond: но- HO Sugar: Type of glycosidic bond: HO- Sugar 1 (left): Sugar 2 (right): Name the two monosaccharides that comprise lactose (shown below). Number the carbons. Name the type of glycosidic bond. HOOH OH НО HO HO- OH OH HO- Name the monosaccharide and the type of glycosidic bond in the polysaccharide galactan shown below. OH НОО OH HO- OH OH OH OHarrow_forwardAre these molecules.... conformers? Enantiomers? Diastereomers? Meso compounds?arrow_forwardWhich of the following statements about the molecule below are FALSE? Briefly explain your answer.arrow_forward
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