Organic Chemistry: Principles and Mechanisms (Second Edition)
Organic Chemistry: Principles and Mechanisms (Second Edition)
2nd Edition
ISBN: 9780393663556
Author: Joel Karty
Publisher: W. W. Norton & Company
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Chapter 5, Problem 5.37P
Interpretation Introduction

(a)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule is to be identified.

Concept introduction:

Isomers are molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be the same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is not same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  1

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  2

The given molecule is the non superimposable mirror image of THE original molecule.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  3

These molecules cannot be interconverted by single bond rotation. Hence, the given molecule is not same enantiomer as the original one.

Conclusion

The molecule is not a same enantiomer as the original molecule is determined on the basis of capability of interconversion by single bond rotation.

Interpretation Introduction

(b)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule is to be identified.

Concept introduction:

Isomers are the molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is a same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  4

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  5

The molecule can be converted to original molecule.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  6

Hence, the given molecule is a same enantiomer as the original one.

Conclusion

The molecule is a same enantiomer as the original molecule is determined on the basis of capability of interconversion by single bond rotation.

Interpretation Introduction

(c)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule is to be identified.

Concept introduction:

Isomers are the molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be the same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is not a same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  7

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  8

The molecule cannot be converted to the original molecule by single bond rotation.

Hence, the given molecule is not same enantiomer as the original one.

Conclusion

The molecule is not a same enantiomer as original molecule is determined on the basis of capability of interconversion by single bond rotation.

Interpretation Introduction

(d)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule is to be identified.

Concept introduction:

Isomers are molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be the same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  9

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  10

The given Newman projection can be converted to zigzag structure as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  11

The molecule can be converted to the original molecule.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  12

Hence, the given molecule is same enantiomer as the original one.

Conclusion

The molecule is a same enantiomer as original molecule is determined by converting Newman projection to zigzag structure.

Interpretation Introduction

(e)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule is to be identified.

Concept introduction:

Isomers are molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be the same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is not a same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  13

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  14

The given Newman projection can be converted to zigzag structure as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  15

The given molecule is a nonsuperimposable mirror image of the original molecule.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  16

These molecules cannot be interconverted by single bond rotation. Hence, the given molecule is not same enantiomer as the original one.

Conclusion

The molecule is a not the same enantiomer as the original molecule is determined by converting Newman projection to zigzag structure.

Interpretation Introduction

(f)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule it is to be identified.

Concept introduction:

Isomers are molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other. In Fischer projection, the horizontal bonds point towards the observer and are denoted as wedge bond in the zigzag structure.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is a same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  17

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  18

The given Fischer projection can be converted to zigzag structure as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  19

Hence, the given molecule is a same enantiomer as the original one.

Conclusion

The molecule is not a same enantiomer as the original molecule is determined by converting Fischer projection to zigzag structure.

Interpretation Introduction

(e)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule is to be identified.

Concept introduction:

Isomers are molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be the same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other. In Fischer projection, the horizontal bonds point toward the observer and are denoted as wedge bond in the zigzag structure.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is not a same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  20

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  21

The given Fischer projection can be converted to zigzag structure as shown below:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  22

The given molecule is a nonsuperimposable mirror image of the original molecule.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  23

These molecules cannot be interconverted by single bond rotation. Hence, the given molecule is not same enantiomer as the original one.

Conclusion

The molecule is not a same enantiomer as the original molecule is determined by converting Fischer projection to zigzag structure.

Interpretation Introduction

(g)

Interpretation:

The given molecule is same or different enantiomer of the shown original molecule it is to be identified.

Concept introduction:

Isomers are the molecules having same connectivity. Enantiomers are nonsuperimposable mirror images. If the molecules can be interconverted by one or more single bond rotation, then they are said to be the same enantiomer or identical molecules. If the molecules are not able to interconvert, then they are enantiomers of each other.

Expert Solution
Check Mark

Answer to Problem 5.37P

The given molecule is not a same enantiomer as the original one.

Explanation of Solution

The given original enantiomer is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  24

The molecule which is to be compared is:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  25

This molecule can be converted to original molecule by single bond rotation.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  26

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.37P , additional homework tip  27

Hence, the given molecule is same enantiomer as the original one.

Conclusion

The molecule is a same enantiomer as the original molecule is determined on the basis of capability of interconversion by single bond rotation.

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Chapter 5 Solutions

Organic Chemistry: Principles and Mechanisms (Second Edition)

Ch. 5 - Prob. 5.11PCh. 5 - Prob. 5.12PCh. 5 - Prob. 5.13PCh. 5 - Prob. 5.14PCh. 5 - Prob. 5.15PCh. 5 - Prob. 5.16PCh. 5 - Prob. 5.17PCh. 5 - Prob. 5.18PCh. 5 - Prob. 5.19PCh. 5 - Prob. 5.20PCh. 5 - Prob. 5.21PCh. 5 - Prob. 5.22PCh. 5 - Prob. 5.23PCh. 5 - Prob. 5.24PCh. 5 - Prob. 5.25PCh. 5 - Prob. 5.26PCh. 5 - Prob. 5.27PCh. 5 - Prob. 5.28PCh. 5 - Prob. 5.29PCh. 5 - Prob. 5.30PCh. 5 - Prob. 5.31PCh. 5 - Prob. 5.32PCh. 5 - Prob. 5.33PCh. 5 - Prob. 5.34PCh. 5 - Prob. 5.35PCh. 5 - Prob. 5.36PCh. 5 - Prob. 5.37PCh. 5 - Prob. 5.38PCh. 5 - Prob. 5.39PCh. 5 - Prob. 5.40PCh. 5 - Prob. 5.41PCh. 5 - Prob. 5.42PCh. 5 - Prob. 5.43PCh. 5 - Prob. 5.44PCh. 5 - Prob. 5.45PCh. 5 - Prob. 5.46PCh. 5 - Prob. 5.47PCh. 5 - Prob. 5.48PCh. 5 - Prob. 5.49PCh. 5 - Prob. 5.50PCh. 5 - Prob. 5.51PCh. 5 - Prob. 5.52PCh. 5 - Prob. 5.53PCh. 5 - Prob. 5.54PCh. 5 - Prob. 5.55PCh. 5 - Prob. 5.56PCh. 5 - Prob. 5.57PCh. 5 - Prob. 5.58PCh. 5 - Prob. 5.59PCh. 5 - Prob. 5.60PCh. 5 - Prob. 5.61PCh. 5 - Prob. 5.62PCh. 5 - Prob. 5.63PCh. 5 - Prob. 5.64PCh. 5 - Prob. 5.65PCh. 5 - Prob. 5.66PCh. 5 - Prob. 5.67PCh. 5 - Prob. 5.68PCh. 5 - Prob. 5.69PCh. 5 - Prob. 5.70PCh. 5 - Prob. 5.71PCh. 5 - Prob. 5.72PCh. 5 - Prob. 5.73PCh. 5 - Prob. 5.74PCh. 5 - Prob. 5.75PCh. 5 - Prob. 5.76PCh. 5 - Prob. 5.77PCh. 5 - Prob. 5.78PCh. 5 - Prob. 5.79PCh. 5 - Prob. 5.1YTCh. 5 - Prob. 5.2YTCh. 5 - Prob. 5.3YTCh. 5 - Prob. 5.4YTCh. 5 - Prob. 5.5YTCh. 5 - Prob. 5.6YTCh. 5 - Prob. 5.7YTCh. 5 - Prob. 5.8YTCh. 5 - Prob. 5.9YTCh. 5 - Prob. 5.10YTCh. 5 - Prob. 5.11YTCh. 5 - Prob. 5.12YTCh. 5 - Prob. 5.13YTCh. 5 - Prob. 5.14YTCh. 5 - Prob. 5.15YTCh. 5 - Prob. 5.16YTCh. 5 - Prob. 5.17YT
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