Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
Question
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Chapter 24, Problem 24.1P
Interpretation Introduction

(a)

Interpretation:

The Fischer projections for the given molecule are to be stated.

Concept introduction:

Fischer projections is a two dimensional representation of organic compounds. It was proposed to represent glucose molecules. The carbon chain is represented vertically; the hydoxy groups and hydrogen atoms are represented horizontally, according to their stereochemistry. The aldehyde group is paced at the top of the carbon chain and numbered 1 and the ketone group is usually placed at the carbon -2.

Expert Solution
Check Mark

Answer to Problem 24.1P

The Fischer projections for the given molecule are shown below.

Organic Chemistry, Chapter 24, Problem 24.1P , additional homework tip  1

Explanation of Solution

The structure of the given molecule is shown below.

Organic Chemistry, Chapter 24, Problem 24.1P , additional homework tip  2

Figure 1

In the Fischer projection, the compound, (2R,3S,4S)-2, 3, 4, 5-tetrahydroxypentanoicacid is represented in two-dimension, the substituent on the carbon chain are placed in such a way that stereochemistry remains same. The groups are interchanged simultaneously such that the stereochemistry of carbon atoms in the second structure also remains same as shown below.

Organic Chemistry, Chapter 24, Problem 24.1P , additional homework tip  3

Figure 2

Conclusion

The Fischer projections of (2R,3S,4S)-2, 3, 4, 5-tetrahydroxypentanoicacid are shown in Figure 2.

Interpretation Introduction

(b)

Interpretation:

The Fischer projections for (S)-2-butanol are to be stated.

Concept introduction:

Fischer projections is a two dimensional representation of organic compounds. It was proposed to represent glucose molecules. The carbon chain is represented vertically; the hydoxy groups and hydrogen atoms are represented horizontally, according to their stereochemistry. The aldehyde group is paced at the top of the carbon chain and numbered 1 and the ketone group is usually placed at the carbon -2.

Expert Solution
Check Mark

Answer to Problem 24.1P

The Fischer projections for (S)-2-butanol are shown below.

Organic Chemistry, Chapter 24, Problem 24.1P , additional homework tip  4

Explanation of Solution

The structure of (S)-2-butanol is shown below.

Organic Chemistry, Chapter 24, Problem 24.1P , additional homework tip  5

Figure 3

In the Fischer projection, the compound, (S)-2-butanol is represented in two-dimension, the substituent on the carbon chain are placed in such a way that stereochemistry remains same. The groups are interchanged simultaneously in a clockwise direction such that the stereochemistry of carbon atoms in the second structure also remains same as shown below.

Organic Chemistry, Chapter 24, Problem 24.1P , additional homework tip  6

Figure 4

Conclusion

The Fischer projections of (S)-2-butanol are shown in Figure 4.

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