a) 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.

Question

(a) Sketch the 'H NMR of the following chemical including the approximate chemical shifts, the multiplicity (splitting) of all signals and the integration (b) How many signals would you expect in the 13C NMR? CH3

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 25.3, Problem 6P

Interpretation Introduction

a)

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)

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)

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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(a) Sketch the 'H NMR of the following chemical including the approximate chemical shifts, the multiplicity (splitting) of all signals and the integration (b) How many signals would you expect in the 13C NMR? CH3

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Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 25.3, Problem 6P

Interpretation Introduction

a)

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)

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)

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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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 25.3, Problem 6P

Interpretation Introduction

a)

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)

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)

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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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 25.3, Problem 6P

Interpretation Introduction

a)

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)

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)

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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Answer 5

Chapter 25.3, Problem 6P

Interpretation Introduction

a)

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)

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)

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.

Answer 6

Chapter 25.3, Problem 6P

Interpretation Introduction

a)

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.

Answer 7

Chapter 25.3, Problem 6P

Interpretation Introduction

a)

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.

Answer 8

Interpretation Introduction

b)

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.

Answer 9

Interpretation Introduction

b)

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.

Answer 10

Interpretation Introduction

c)

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.

Answer 11

Interpretation Introduction

c)

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.

Answer 12

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Answer 23

Ch. 25.1 - Prob. 1P Ch. 25.2 - Prob. 2P Ch. 25.2 - Prob. 3P Ch. 25.2 - Prob. 4P Ch. 25.2 - Prob. 5P Ch. 25.3 - Prob. 6P Ch. 25.3 - Prob. 7P Ch. 25.4 - Prob. 8P Ch. 25.4 - Prob. 9P Ch. 25.4 - Prob. 10P

Solution Summary: The author explains how the configuration as R or S is to be assigned to each chirality center in the monosaccharide given and whether it is a D or L sugar.

Concept explainers

Chapter 25 Solutions