Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
Question
Book Icon
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.

Want to see more full solutions like this?

Subscribe now to access step-by-step solutions to millions of textbook problems written by subject matter experts!
Students have asked these similar questions
Draw the structures that correspond to their IUPAC or common name. (c) 4-mercapto-1-butanol (d) trans-1,3-diethoxycyclopentane
For each pair of compounds, predict which compound has a higher boiling point. then explain why that compound has a higher boiling point. (a) isopropyl bromide and n-butyl bromide (b) isopropyl chloride and tert-butyl bromide (c) 1-bromobutane and 1-chlorobutane
Please answer the three questions below: 1. Representation of molecules looking directly in front of a C-C bond end on (A) Fisher projection (B) Newman projection (C) Sawhorse projection (D) Wedge and dash 2. What products are produced when a carboxylic acid reacts with an alcohol, in the presence of sulfuric acid? (A) an ether (B) an ether + water (C) an ester (D) an ester + water 3. Two different compounds with the same molecular formulas that differ in the way the atoms are connected to each other are called _____. (A) Conformational isomers (B) Configurational isomers (C) Constitutional isomers (D) Stereoisomers
Knowledge Booster
Background pattern image
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Text book image
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Text book image
Introductory Chemistry For Today
Chemistry
ISBN:9781285644561
Author:Seager
Publisher:Cengage
Text book image
Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning