Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Question
Chapter 4, Problem 83P
Interpretation Introduction
Interpretation:
The assigning of configuration of each asymmetric center as R if –OH group is on the right and the configuration is S if the –OH is group in on left side for D-glucose has to be checked.
Concept introduction:
- Asymmetric center is a stereocenter which arises to a compound if any atom is bonded to four different groups.
- The stereo-descriptor for other carbohydrates of having more than one chiral center will be evaluated by the location of –OH group (right or left) of farthest chiral carbon from the carbonyl group. Such as,
If the –OH group is located in right side then, the carbohydrate is a D-sugar.
If the –OH group is located in left side then, the carbohydrate is a L-sugar.
- Configuration of a molecule: The configurations of a molecule arise due to the spatial arrangement of atoms. The configuration can be assigned by following CIP rules as follows.
- Assign numbering to the groups which are bonded to the chiral carbon based on the molecular weight and electronegativity.
- If the sequence of the numbering follows clockwise direction the chiral atom is assigned as R configuration.
- If the sequence of the numbering follows anticlockwise direction the chiral atom is assigned as S configuration.
- If the least priority group is on horizontal line in the fisher projection, then configuration is inverted to the obtained configuration from the above CIP rule which means R configuration becomes S and vice versa.
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A student decided that the configuration of the asymmetric centers in a sugar such as d-glucose could be determined rapidly by simply assigning the R configuration to an asymmetric center with an OH group on the right and the S configuration to an asymmetric center with an OH group on the left. Is he correct?
1) Below you are given the structures of the disaccharides lactose and trehalose.
он
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Draw the structure of the disaccharide maltose (-D-glucopyranosyl (1→4)-D-glucopyranose). Indicate with arrows the reducing end and the acetal functional group.
Chapter 4 Solutions
Organic Chemistry
Ch. 4.1 - Prob. 2PCh. 4.1 - Prob. 3PCh. 4.1 - Prob. 4PCh. 4.1 - Prob. 5PCh. 4.1 - Which of the roll owing compounds have a dipole...Ch. 4.2 - Prob. 7PCh. 4.3 - Prob. 8PCh. 4.4 - Prob. 10PCh. 4.4 - Prob. 11PCh. 4.6 - Prob. 12P
Ch. 4.7 - Prob. 14PCh. 4.7 - Prob. 16PCh. 4.7 - Prob. 17PCh. 4.7 - Draw a perspective formula for each or the...Ch. 4.8 - Prob. 20PCh. 4.9 - Prob. 21PCh. 4.9 - (S)-(+)-Monosodium glutamate (MSG) is a flavor...Ch. 4.10 - Prob. 23PCh. 4.10 - Prob. 24PCh. 4.11 - Prob. 26PCh. 4.11 - Prob. 27PCh. 4.11 - Prob. 28PCh. 4.11 - The stereoisomer of cholesterol found in nature is...Ch. 4.11 - Prob. 30PCh. 4.12 - Prob. 31PCh. 4.12 - Draw all possible stereoisomers for each of the...Ch. 4.12 - Prob. 33PCh. 4.12 - Of all the possible cyclooctanes that have one...Ch. 4.12 - Prob. 35PCh. 4.12 - Prob. 36PCh. 4.13 - Which of the following compounds has a...Ch. 4.13 - Prob. 39PCh. 4.14 - Prob. 40PCh. 4.14 - Name the isomers you drew in Problem 52.Ch. 4.14 - Chloramphenicol is a broad-spectrum antibiotic...Ch. 4.14 - Draw a perspective formula for each of the...Ch. 4.14 - Name the following:Ch. 4.14 - Prob. 45PCh. 4.14 - Prob. 48PCh. 4.14 - Prob. 50PCh. 4.15 - Limonene exists as two different stereoisomers....Ch. 4.16 - Prob. 52PCh. 4 - a. Draw three constitutional isomers with...Ch. 4 - Prob. 53PCh. 4 - Prob. 54PCh. 4 - Which of the following has an asymmetric center?...Ch. 4 - Prob. 56PCh. 4 - Prob. 57PCh. 4 - Prob. 58PCh. 4 - Which of the following are optically active?Ch. 4 - Prob. 60PCh. 4 - Prob. 61PCh. 4 - Which of the following has an achiral...Ch. 4 - Prob. 63PCh. 4 - Prob. 64PCh. 4 - Prob. 65PCh. 4 - Prob. 66PCh. 4 - Prob. 67PCh. 4 - Prob. 68PCh. 4 - Prob. 69PCh. 4 - Prob. 70PCh. 4 - Prob. 71PCh. 4 - Prob. 72PCh. 4 - Prob. 73PCh. 4 - a. Draw all the isomers with molecular formula...Ch. 4 - Prob. 75PCh. 4 - Prob. 76PCh. 4 - Draw structures for the following: a....Ch. 4 - Prob. 78PCh. 4 - Prob. 79PCh. 4 - Prob. 80PCh. 4 - a. Using the wedge-and-dash notation, draw the...Ch. 4 - Prob. 82PCh. 4 - Prob. 83PCh. 4 - Prob. 84PCh. 4 - a. Draw the two chair conformers for each of the...Ch. 4 - Prob. 86PCh. 4 - Is the following compound optically active?
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