Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 28, Problem 28.40P

Convert each compound to a Fischer projection and label each stereogenic center as R or S

a. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  1 c. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  2 e. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  3 g. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  4

b. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  5 d. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  6 f. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  7 h. Chapter 28, Problem 28.40P, Convert each compound to a Fischer projection and label each stereogenic center as R or S a. c. e. , example  8

Expert Solution
Check Mark
Interpretation Introduction

(a)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center of a compound is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  1

The stereogenic center of a compound is labeled as S.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  2

Figure 1

The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  3

Figure 2

In the compound, COOH, Br, CH3 and H substituents are attached to carbon atom. The atomic number of C, Br and H is 6, 35 and 1 respectively. Thus, first priority is given to Br substituent. There are two substituents i.e. COOH, CH3 are connected to the stereogenic centre through the carbon atom. Now, the priority is given on the basis of atomic number of second atom which is attached to the carbon atom. The carbon of COOH is connected the oxygen atom and the atomic number of oxygen is 8 while the another carbon atom of CH3 is connected the carbon atom and the atomic number of carbon is 6. Thus, the second priority is given to COOH substituent then third priority to CH3 substituent. Complete the circle in decreasing order of priority from 123 is shown below

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  4

Figure 3

The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as S.

Hence, the Fischer projection of given compound is shown in Figure 2 and the stereogenic center of a compound is labeled as S.

Conclusion

The Fischer projection of given compound is shown in Figure 2 and the stereogenic center of a compound is labeled as S.

Expert Solution
Check Mark
Interpretation Introduction

(b)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center of a compound is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  5

The stereogenic center of a compound is labeled as S.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  6

Figure 4

In the given compound, the horizontal line is behind the plane and vertical line is in front of the plane. Therefore, the given compound is rotated and redrawn as shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  7

Figure 5

The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  8

Figure 6

In the compound, Cl, Br, CH3 and H substituents are attached to carbon atom. The atomic number of C, Br and H is 6, 35 and 1 respectively. Thus, first priority is given to Br substituent. There are two substituents i.e. Cl, CH3 are connected to the stereogenic centre through the carbon atom. The second priority is given to Cl substituent then third priority to CH3 substituent. Complete the circle in decreasing order of priority from 123 is shown below

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  9

Figure 7

The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as S.

Hence, the Fischer projection of given compound is shown in Figure 6 and the stereogenic center of a compound is labeled as S.

Conclusion

The Fischer projection of given compound is shown in Figure 6 and the stereogenic center of a compound is labeled as S.

Expert Solution
Check Mark
Interpretation Introduction

(c)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  10

The stereogenic center of a compound is labeled as S.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  11

Figure 8

The given compound is redrawn. The horizontal and vertical line represents the bonds in front of the plane and behind the plane is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  12

Figure 9

Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  13

Figure 10

In the compound, CH3CH2O, CH3,CH2CH3 and OCH3 substituents are attached to carbon atom. The atomic number of C and O is 6 and 8 respectively. Thus, first priority is given to O containing substituent. There are two substituents i.e. CH3CH2O, OCH3 are connected to the stereogenic centre through the oxygen atom and third atom in these substituent is also same(carbon) Now, the priority is given on the basis of atomic number of third atom. The third atom of CH3CH2O is carbon atom and the atomic number of carbon is 6 while the third atom of OCH3 is connected to the hydrogen atom and the atomic number of hydrogen is 1. Thus, the first and second priorities are given to CH3CH2O and OCH3 substituent.

Similarly, the third and forth priorities are given to CH2CH3 and CH3 substituents. Complete the circle in decreasing order of priority from 123 is shown below

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  14

Figure 11

The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as S.

Hence, the Fischer projection of given compound is shown in Figure 10 and the stereogenic center of a compound is labeled as S.

Conclusion

The Fischer projection of given compound is shown in Figure 10 and the stereogenic center of a compound is labeled as S.

Expert Solution
Check Mark
Interpretation Introduction

(d)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  15

The stereogenic center of a compound is labeled as S.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  16

Figure 12

The given compound is redrawn. The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  17

Figure 13

Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  18

Figure 14

In the compound, Cl, Br, CH2CH3 and H substituents are attached to carbon atom. The atomic number of C, Br and Cl is 6, 35 and 17 respectively. Thus, first priority is given to Cl substituent. Thus, the second priority is given to Br substituent then third priority to CH2CH3 substituent. Complete the circle in decreasing order of priority from 123 is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  19

Figure 15

The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as S.

Hence, the Fischer projection of given compound is shown in Figure 14 and the stereogenic center of a compound is labeled as S.

Conclusion

The Fischer projection of given compound is shown in Figure 14 and the stereogenic center of a compound is labeled as S.

Expert Solution
Check Mark
Interpretation Introduction

(e)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  20

The stereogenic center of a compound are labeled as 2S and 3S.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  21

Figure 16

The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  22

Figure 17

In the compound, -CH(Cl)(CH2CH3), Br, CH3 and H substituents are attached to C2 atom. The atomic number of C, Br and H is 6, 35 and 1 respectively. Thus, first priority is given to Br substituent. Thus, the second and third priorities are given to -CH(Cl)(CH2CH3), CH3 substituents. Complete the circle in decreasing order of priority from 123. The circle rotates in the clockwise direction, configuration at C2 would be R but forth priority should be come away from viewer. Therefore the configuration gets reversed. Thus, configuration at C2 is labeled as S

Similarly, in the C3 atom, the first and second priorities are given to Cl and -CH(Br)(CH2CH3). Complete the circle in decreasing order of priority from 123 The circle rotates in the clockwise direction, configuration at C3 would be R but forth priority should be come away from viewer. Therefore the configuration gets reversed. Thus, configuration at C3 is labeled as S. The priorities at C2 and C3 are shown below

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  23

Figure 18

Hence, the Fischer projection of given compound is shown in Figure 17 and the stereogenic center of a compound are labeled as 2S and 3S.

Conclusion

The Fischer projection of given compound is shown in Figure 17 and the stereogenic center of a compound are labeled as 2S and 3S.

Expert Solution
Check Mark
Interpretation Introduction

(f)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center of a compound is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  24

The stereogenic centers of the compound are labeled as 1S and 2R.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  25

Figure 19

In the given compound, the horizontal line is behind the plane and vertical line is in front of the plane. Therefore, the given compound is rotated and redrawn as shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  26

Figure 20

The horizontal and vertical line represents the bonds in front of the plane and behind the plane. Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  27

Figure 21

In the compound, Cl, Br, CH(Br)(Cl) and H substituents are attached to first carbon atom. The atomic number of C, Br and H is 6, 35 and 1 respectively. Thus, first priority is given to Br substituent. There are two substituents i.e. Cl, CH(Br)(Cl) are connected to the stereogenic centre through the carbon atom. The second priority is given to Cl substituent then third priority to CH(Br)(Cl) substituent. Complete the circle in decreasing order of priority from 123 is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  28

Figure 22

The circle rotates in the anticlockwise direction. Thus, the given compound is labeled as S.

Similarly, in the compound, Cl, Br, CH(Br)(Cl) and H substituents are attached to second carbon atom. The atomic number of C, Br and H is 6, 35 and 1 respectively. Thus, first priority is given to Br substituent. There are two substituents i.e. Cl, CH(Br)(Cl) are connected to the stereogenic centre through the carbon atom. The second priority is given to Cl substituent then third priority to CH(Br)(Cl) substituent. Complete the circle in decreasing order of priority from 123 is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  29

Figure 23

The circle rotates in the clockwise direction. Thus, the given compound is labeled as R.

Hence, the Fischer projection of given compound is shown in Figure 21 and the stereogenic centers of the compound are labeled as 1S and 2R.

Conclusion

The Fischer projection of given compound is shown in Figure 21 and the stereogenic centers of the compound are labeled as 1S and 2R.

Expert Solution
Check Mark
Interpretation Introduction

(g)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  30

The stereogenic center of a compound as 2S and 3S.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  31

Figure 24

The given compound is redrawn. The horizontal and vertical line represents the bonds in front of the plane and behind the plane as shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  32

Figure 25

Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  33

Figure 26

In the compound, -CH(Br)(CH2CH3), Br, CH3 and H substituents are attached to C2 atom. The atomic number of C, Br and H is 6, 35 and 1 respectively. Thus, first priority is given to Br substituent. Thus, the second and third priorities are given to -CH(Br)(CH2CH3), CH3 substituents. Complete the circle in decreasing order of priority from 123. The circle rotates in the clockwise direction, configuration at C2 would be R but forth priority should be come away from viewer. Therefore the configuration gets reversed. Thus, configuration at C2 is labeled as S

Similarly, in the C3 atom, the first and second priorities are given to Br and -CH(Br)(CH2CH3). Complete the circle in decreasing order of priority from 123 The circle rotates in the clockwise direction, configuration at C3 would be R but forth priority should be come away from viewer. Therefore the configuration gets reversed. Thus, configuration at C3 is labeled as S. The priorities at C2 and C3 are shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  34

Figure 27

Hence, the Fischer projection of given compound is shown in Figure 26 and the stereogenic center of a compound are labeled as 2S and 3S.

Conclusion

The Fischer projection of given compound is shown in Figure 26 and the stereogenic center of a compound are labeled as 2S and 3S.

Expert Solution
Check Mark
Interpretation Introduction

(h)

Interpretation: The given compound is to be converted into Fischer projection and the stereogenic center is to be labeled as R or S.

Concept introduction: In Fischer projection formula, the horizontal and vertical line represents the bonds that are present above and below the plane, respectively. The verticals bonds are represented as dashed wedge and horizontal bonds as dark wedge.

Answer to Problem 28.40P

The Fischer projection of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  35

The stereogenic center of a compound are labeled as 2S, 3S and 3R.

Explanation of Solution

The structure of given compound is,

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  36

Figure 28

The Fischer projection is drawn by converting the stable staggered conformation into less stable eclipsed conformation. The bonds present below the plane in eclipsed conformation are placed on the left side of the horizontal line in Fischer projection formula as shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  37

Figure 29

Hence, the Fischer projection of given compound is shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  38

Figure 30

In the compound, -CH(OH)CHOH(CH2OH), OH, CHO and H substituents are attached to C2 atom. Thus, the first and second priorities are given to  OH, CHO substituents then third priority is given to -CH(OH)CHOH(CH2OH). Complete the circle in decreasing order of priority from 123. The circle rotates in the clockwise direction, configuration at C2 would be R but forth priority should be come away from viewer. Thus, configuration at C2 is labeled as S.

Similarly, in the C3 atom, the first and second priorities are given to OH and -CHOH(CHO). Complete the circle in decreasing order of priority from 123 The circle rotates in the clockwise direction, configuration at C3 would be R but forth priority should be come away from viewer. Therefore the configuration gets reversed. Thus, configuration at C3 is labeled as S.

Similarly, in the C4 atom, the first and second priorities are given to OH and -CHO(CHOH)2. Complete the circle in decreasing order of priority from 123. The circle rotates in the anticlockwise direction, configuration at C4 would be S but forth priority should be come away from viewer. Therefore the configuration gets reversed. Thus, configuration at C4 is labeled as R. The priorities at C2, C3 and C4 are shown below.

Organic Chemistry, Chapter 28, Problem 28.40P , additional homework tip  39

Figure 31

Hence, the Fischer projection of given compound is shown in Figure 30 and the stereogenic center of a compound are labeled as 2S, 3S and 3R.

Conclusion

The Fischer projection of given compound is shown in Figure 30 and the stereogenic center of a compound are labeled as 2S, 3S and 3R.

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
Problem 5.16 Label each stereogenic center as R or S. e. HO, HO H f.
Draw all stereoisomers formed when each alkene is treated with mCPBA.
Give the IUPAC name for each compound, including the R, S designation for each stereogenic center. In a. b. C.

Chapter 28 Solutions

Organic Chemistry

Ch. 28 - Prob. 28.11PCh. 28 - Prob. 28.12PCh. 28 - Prob. 28.13PCh. 28 - Prob. 28.14PCh. 28 - Prob. 28.15PCh. 28 - Prob. 28.16PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.18PCh. 28 - Prob. 28.19PCh. 28 - Prob. 28.20PCh. 28 - Prob. 28.21PCh. 28 - Draw the products formed when D-arabinose is...Ch. 28 - Prob. 28.23PCh. 28 - Prob. 28.24PCh. 28 - Prob. 28.25PCh. 28 - Prob. 28.26PCh. 28 - Prob. 28.27PCh. 28 - Prob. 28.28PCh. 28 - Prob. 28.29PCh. 28 - Prob. 28.30PCh. 28 - Prob. 28.31PCh. 28 - Prob. 28.32PCh. 28 - Prob. 28.33PCh. 28 - Prob. 28.34PCh. 28 - Problem-28.35 Draw the structures of the...Ch. 28 - Prob. 28.36PCh. 28 - 28.37 Convert each ball-and-stick model to a...Ch. 28 - Prob. 28.38PCh. 28 - Prob. 28.39PCh. 28 - Convert each compound to a Fischer projection and...Ch. 28 - Prob. 28.41PCh. 28 - Prob. 28.42PCh. 28 - Prob. 28.43PCh. 28 - Prob. 28.44PCh. 28 - Prob. 28.45PCh. 28 - Draw both pyranose anomers of each aldohexose...Ch. 28 - Prob. 28.47PCh. 28 - Prob. 28.48PCh. 28 - Prob. 28.49PCh. 28 - Prob. 28.50PCh. 28 - Prob. 28.51PCh. 28 - Prob. 28.52PCh. 28 - Prob. 28.53PCh. 28 - What products are formed when each compound is...Ch. 28 - Prob. 28.55PCh. 28 - Prob. 28.56PCh. 28 - Prob. 28.57PCh. 28 - Prob. 28.58PCh. 28 - 28.58 Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.60PCh. 28 - Prob. 28.61PCh. 28 - Prob. 28.62PCh. 28 - Prob. 28.63PCh. 28 - Prob. 28.64PCh. 28 - Prob. 28.65PCh. 28 - Prob. 28.66PCh. 28 - Prob. 28.67PCh. 28 - Prob. 28.68PCh. 28 - Prob. 28.69PCh. 28 - Prob. 28.70PCh. 28 - Prob. 28.71PCh. 28 - Prob. 28.72PCh. 28 - Prob. 28.73PCh. 28 - Prob. 28.74PCh. 28 - Prob. 28.75PCh. 28 - Prob. 28.76PCh. 28 - Prob. 28.77PCh. 28 - Draw a stepwise mechanism for the following...Ch. 28 - Prob. 28.79P
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
Text book image
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Text book image
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Text book image
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Text book image
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Text book image
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY
Nomenclature: Crash Course Chemistry #44; Author: CrashCourse;https://www.youtube.com/watch?v=U7wavimfNFE;License: Standard YouTube License, CC-BY