Organic Chemistry
Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 25.3, Problem 6P
Interpretation Introduction

a)

Organic Chemistry, Chapter 25.3, Problem 6P , additional homework tip  1

Interpretation:

The configuration as R or S is to be assigned to each chirality center in the monosaccharide given and whether it is a D sugar or L sugar is to be stated.

Concept introduction:

In Fischer projection formula, a tetrahedral carbon is represented by two crossed lines. The horizontal line represents bonds coming out of the page and vertical lines represent bonds moving in to the page.

For assigning R or S configuration, the four groups attached to the chiral center are arranged in the order of priority by applying sequence rules. The molecule is then oriented in such a way that the group of lowest priority points away from the viewer. If the arrangement of highest priority to second highest priority to third highest priority is clockwise then R configuration is assigned. If the arrangement of highest priority to second highest priority to third highest priority is counterclockwise then S configuration is assigned.

In Fischer projections, D sugars have the hydroxyl group on right at the farthest chirality center and L sugars have this hydroxyl group on left.

To assign:

The configuration as R or S to each chirality center in the monosaccharide given and to state whether it is a D sugar or L sugar.

Interpretation Introduction

b)

Organic Chemistry, Chapter 25.3, Problem 6P , additional homework tip  2

Interpretation:

The configuration as R or S is to be assigned to each chirality center in the monosaccharide given and whether it is a D sugar or L sugar is to be stated.

Concept introduction:

For assigning R or S configuration, the four groups attached to the chiral center are arranged in the order of priority by applying sequence rules. The molecule is then oriented in such a way that the group of lowest priority points away from the viewer. If the arrangement of highest priority to second highest priority to third highest priority is clockwise then R configuration is assigned. If the arrangement of highest priority to second highest priority to third highest priority is counterclockwise then S configuration is assigned.

To assign:

The configuration as R or S to each chirality center in the monosaccharide given and to state whether it is a D sugar or L sugar.

Interpretation Introduction

c)

Organic Chemistry, Chapter 25.3, Problem 6P , additional homework tip  3

Interpretation:

The configuration as R or S is to be assigned to each chirality center in the monosaccharide given and whether it is a D sugar or L sugar is to be stated.

Concept introduction:

In Fischer projection formula, a tetrahedral carbon is represented by two crossed lines. The horizontal line represents bonds coming out of the page and vertical lines represent bonds moving in to the page.

For assigning R or S configuration, the four groups attached to the chiral center are arranged in the order of priority by applying sequence rules. The molecule is then oriented in such a way that the group of lowest priority points away from the viewer. If the arrangement of highest priority to second highest priority to third highest priority is clockwise then R configuration is assigned. If the arrangement of highest priority to second highest priority to third highest priority is counterclockwise then S configuration is assigned.

To assign:

The configuration as R or S to each chirality center in the monosaccharide given and to state whether it is a D sugar or L sugar.

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Assign r or s configuration to each chirality center of the following monosaccharide?
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Draw the following monosaccharides, using chair conformations for the pyranoses andHaworth projections for the furanoses.(a) a-d-mannopyranose (C2 epimer of glucose)(b) b-d-galactopyranose (C4 epimer of glucose)(c) b-d-allopyranose (C3 epimer of glucose)(d) a-d-arabinofuranose(e) b-d-ribofuranose (C2 epimer of arabinose)

Chapter 25 Solutions

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