Organic Chemistry
Organic Chemistry
4th Edition
ISBN: 9780073402772
Author: Janice G. Smith
Publisher: MCG
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Chapter 5, Problem 5.51P
Interpretation Introduction

(a)

Interpretation: The structure of naturally occurring ()-ephedrine, which has the 1R,2S configuration is to be drawn.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termedaschiralcenter or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers, whereas two compounds which are neither superimposable nor mirror images to each other are known as diastereomer.

Expert Solution
Check Mark

Answer to Problem 5.51P

The structure of naturally occurring ()-ephedrine, which has the 1R,2S configuration is drawn below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  1

Explanation of Solution

The structure of given compoundis shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  2

Figure 1

The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritizedon the basis ofatomic number of their atoms. The group that contains atom with a the higher atomic number is given higher priority. The configuration of the compound is R and S when the circle rotates in a clockwise and anticlockwise direction respectively.

The configuration at the first stereocenter of ()-ephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  3

Figure 2

The above structure implies that the configuration at the first stereocenter of ()-ephedrine is R.

The configuration at the second stereocenter of ()-ephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  4

Figure 3

The above structure implies that the configuration at the second stereocenter of ()-ephedrine is S.

The configuration at both the stereocenters of ()-ephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  5

Figure 4

The configurations at the first and second stereocenters of ()-ephedrine are R and S respectively.

Conclusion

The structure of naturally occurring ()-ephedrine, which has the 1R,2S configuration is drawn in Figure 4.

Interpretation Introduction

(b)

Interpretation: The structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration is to be drawn.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termedaschiralcenter or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers, whereas two compounds which are neither superimposable nor mirror images to each other are known as diastereomer.

Expert Solution
Check Mark

Answer to Problem 5.51P

The structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration is drawn below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  6

Explanation of Solution

The structure of naturally occurring pseudoephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  7

Figure 5

The stereochemistry of the compound is determined by prioritizing the groups attached to its stereogenic center. The groups are prioritizedon the basis of atomic number of their atoms. The group that contain atom with higher atomic number is givenhigher priority. Complete the circle in decreasing order of priorityfrom 123. The configuration of the compound is R and S when the circle rotates in clockwise and anticlockwise direction respectively.

The configuration at first chiral center of (+)-pseudoephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  8

Figure 6

The above structure implies that the configuration at the first stereocenter of (+)-pseudoephedrine is S.

The configuration at the second chiral center of (+)-pseudoephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  9

Figure 7

The above structure implies that the configuration at the second stereocenter of (+)-pseudoephedrine is S.

The configuration at the first and second chiral centers of (+)-pseudoephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  10

Figure 8

The configurations at the first and second carbon atoms of (+)-pseudoephedrine are S,S.

Conclusion

The structure of naturally occurring (+)-pseudoephedrine, which has the 1S,2S configuration is drawn in Figure 8.

Interpretation Introduction

(c)

Interpretation: The relationship between ephedrine and pseudoephedrine is to be identified.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termedaschiralcenter or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers, whereas two compounds which are neither superimposable nor mirror images to each other are known as diastereomer.

Expert Solution
Check Mark

Answer to Problem 5.51P

Ephedrine and pseudoephedrine are related as diastereomers.

Explanation of Solution

The relationship between ephedrine and pseudoephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  11

Figure 9

One stereocenter in both the compounds has opposite configuration, while the other stereogenic center has the same configuration. Therefore, both the compounds are related as diastereomer.

Conclusion

Ephedrine and pseudoephedrine are related as diastereomers.

Interpretation Introduction

(d)

Interpretation: All the stereoisomers of ()-ephedrine and (+)-pseudoephedrine are to be drawn along with their R,S designation for all stereogenic centers.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termedaschiralcenter or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers, whereas two compounds which are neither superimposable nor mirror images to each other are known as diastereomer.

Expert Solution
Check Mark

Answer to Problem 5.51P

The stereoisomers of ()-ephedrine and (+)-pseudoephedrine along with their R,S designation for all stereogenic centers are drawn below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  12

Explanation of Solution

The stereoisomers of ()-ephedrine and (+)-pseudoephedrine along with their R,S designation for all stereogenic centers are shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  13

Figure 10

Both the stereoisomers have two stereocenters. One stereocenter in both the compounds has the same configuration, while the other stereocenter in both the compounds has opposite configuration.

Conclusion

The stereoisomers of ()-ephedrine and (+)-pseudoephedrine along with their R,S designation for all stereogenic centers are drawn in Figure 10.

Interpretation Introduction

(e)

Interpretation: The relationship between each compound drawn in part (d) and ()-ephedrine is to be identified.

Concept introduction: A compound exhibits number of stereoisomers when it contains more than one stereogenic centers. The maximum number of stereoisomers a compound with n number of stereogenic centers can show is 2n. A carbon atom which is bonded to four different groups is termedaschiralcenter or stereogenic center. Two compounds which are non-superimposable mirror images of each other are known as enantiomers, whereas two compounds which are neither superimposable nor mirror images of each other are known as diastereomer.

Expert Solution
Check Mark

Answer to Problem 5.51P

The relationship between each compound drawn in part (d) and ()-ephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  14

Explanation of Solution

The relationship between each compound drawn in part (d) and ()-ephedrine is shown below.

Organic Chemistry, Chapter 5, Problem 5.51P , additional homework tip  15

Figure 11

The compounds ()-ephedrine and (+)-ephedrine are related to each other as enantiomer, while the compounds ()-ephedrine and (+)-pseudoephedrine are related to each other as diastereomer.

Conclusion

The relationship between each compound drawn in part (d) and ()-ephedrine is shown in Figure 11.

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Chapter 5 Solutions

Organic Chemistry

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