a) Interpretation: Fischer projections of the following molecules are to be given. The S enantiomer of 2-bromobutane. 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 show: Fischer projections of the following molecules. The S enantiomer of 2-bromobutane.

Question

The following compound has two asymmetric centers and four stereoisomers. Two of these are d-erythrose and d-threose, which are naturally occurring sugars. The configuration of d-erythrose is (2R,3R), and the configuration of d-threose is (2S,3R). a. Which structure represents d-erythrose? b. Which represents d-threose?

Answer 1

Question

Chapter 25.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 2-bromobutane.

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 show:

Fischer projections of the following molecules.

The S enantiomer of 2-bromobutane.

Interpretation Introduction

b)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of alanine.

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 show:

Fischer projections of the following molecules.

The R enantiomer of alanine.

Interpretation Introduction

c)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of 2-hydroxypropionic acid.

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 show:

Fischer projections of the following molecules.

The R enantiomer of 2-hydroxypropionic acid.

Interpretation Introduction

d)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 3-methylhexane.

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 show:

The S enantiomer of 3-methylhexane.

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The following compound has two asymmetric centers and four stereoisomers. Two of these are d-erythrose and d-threose, which are naturally occurring sugars. The configuration of d-erythrose is (2R,3R), and the configuration of d-threose is (2S,3R). a. Which structure represents d-erythrose? b. Which represents d-threose?

The relative configurations of the stereoisomers of tartaric acid were established by the following syntheses:(1) d@(+)@glyceraldehyde T diastereomers A and B (separated)(2) Hydrolysis of A and B using aqueous Ba(OH)2 gave C and D, respectively.(3) HNO3 oxidation of C and D gave (-)@tartaric acid and meso-tartaric acid, respectively.(a) You know the absolute configuration of d-(+)-glyceraldehyde. Use Fischer projections to show the absolute configurations of products A, B, C, and D.(b) Show the absolute configurations of the three stereoisomers of tartaric acid: (+)-tartaric acid, (-)-tartaric acid, andmeso-tartaric acid.

1. Draw stereosiomers using flying wedge representation of tetrose (O=CH-CH(OH)-CH(OH)-CH2OH), and indicate chiral centers using asterisks. 2. Identify enantiomers in #1. 3. Identify diastereoisomers in #1.

Answer 2

Question

Chapter 25.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 2-bromobutane.

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 show:

Fischer projections of the following molecules.

The S enantiomer of 2-bromobutane.

Interpretation Introduction

b)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of alanine.

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 show:

Fischer projections of the following molecules.

The R enantiomer of alanine.

Interpretation Introduction

c)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of 2-hydroxypropionic acid.

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 show:

Fischer projections of the following molecules.

The R enantiomer of 2-hydroxypropionic acid.

Interpretation Introduction

d)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 3-methylhexane.

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 show:

The S enantiomer of 3-methylhexane.

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Answer 3

Question

Chapter 25.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 2-bromobutane.

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 show:

Fischer projections of the following molecules.

The S enantiomer of 2-bromobutane.

Interpretation Introduction

b)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of alanine.

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 show:

Fischer projections of the following molecules.

The R enantiomer of alanine.

Interpretation Introduction

c)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of 2-hydroxypropionic acid.

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 show:

Fischer projections of the following molecules.

The R enantiomer of 2-hydroxypropionic acid.

Interpretation Introduction

d)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 3-methylhexane.

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 show:

The S enantiomer of 3-methylhexane.

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Answer 4

Question

Chapter 25.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 2-bromobutane.

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 show:

Fischer projections of the following molecules.

The S enantiomer of 2-bromobutane.

Interpretation Introduction

b)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of alanine.

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 show:

Fischer projections of the following molecules.

The R enantiomer of alanine.

Interpretation Introduction

c)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of 2-hydroxypropionic acid.

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 show:

Fischer projections of the following molecules.

The R enantiomer of 2-hydroxypropionic acid.

Interpretation Introduction

d)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 3-methylhexane.

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 show:

The S enantiomer of 3-methylhexane.

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Answer 5

Chapter 25.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 2-bromobutane.

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 show:

Fischer projections of the following molecules.

The S enantiomer of 2-bromobutane.

Interpretation Introduction

b)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of alanine.

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 show:

Fischer projections of the following molecules.

The R enantiomer of alanine.

Interpretation Introduction

c)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of 2-hydroxypropionic acid.

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 show:

Fischer projections of the following molecules.

The R enantiomer of 2-hydroxypropionic acid.

Interpretation Introduction

d)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 3-methylhexane.

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 show:

The S enantiomer of 3-methylhexane.

Answer 6

Chapter 25.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 2-bromobutane.

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 show:

Fischer projections of the following molecules.

The S enantiomer of 2-bromobutane.

Answer 7

Chapter 25.SE, Problem 42AP

Interpretation Introduction

a)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 2-bromobutane.

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 show:

Fischer projections of the following molecules.

The S enantiomer of 2-bromobutane.

Answer 8

Interpretation Introduction

b)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of alanine.

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 show:

Fischer projections of the following molecules.

The R enantiomer of alanine.

Answer 9

Interpretation Introduction

b)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of alanine.

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 show:

Fischer projections of the following molecules.

The R enantiomer of alanine.

Answer 10

Interpretation Introduction

c)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of 2-hydroxypropionic acid.

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 show:

Fischer projections of the following molecules.

The R enantiomer of 2-hydroxypropionic acid.

Answer 11

Interpretation Introduction

c)

Interpretation:

Fischer projections of the following molecules are to be given.

The R enantiomer of 2-hydroxypropionic acid.

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 show:

Fischer projections of the following molecules.

The R enantiomer of 2-hydroxypropionic acid.

Answer 12

Interpretation Introduction

d)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 3-methylhexane.

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 show:

The S enantiomer of 3-methylhexane.

Answer 13

Interpretation Introduction

d)

Interpretation:

Fischer projections of the following molecules are to be given.

The S enantiomer of 3-methylhexane.

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 show:

The S enantiomer of 3-methylhexane.

Answer 14

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Answer 25

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

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Chapter 25 Solutions