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 5.1P
Interpretation Introduction

(a)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

Molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image. But not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are superimposable.

Explanation of Solution

Molecules in the given pair are

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  1

In the above pair, both molecules have carbon as the central atom with one fluorine atom and three hydrogen atoms as an attachment. In the left molecule, fluorine is pointing towards the observer and one hydrogen atom is pointing away from the observer while in the second molecule fluorine is pointing away from the observer and one hydrogen atom is pointing towards the observer.

To check the molecule in different orientation the molecule present at right is rotated.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  2

The molecule after the rotation has the exact similar orientation of the atoms as the left molecule in the given pair i.e. all atoms are lined up perfectly.

Thus both the molecules in the given pair are superimposable.

Conclusion

All atoms of both molecules are lined perfectly hence superimposable.

Interpretation Introduction

(b)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

Molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image, but not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are superimposable.

Explanation of Solution

Molecules in the given pair are

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  3

In given pair, both molecules are mirror images of each other. If the molecule at right is rotated, it gives the molecule exactly similar to the left one.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  4

Thus both the molecules in the given pair are superimposable.

Conclusion

All atoms of both the molecules are lined perfectly hence superimposable.

Interpretation Introduction

(c)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

Molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image, but not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are nonsuperimposable.

Explanation of Solution

Molecules in the given pair are:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  5

Two molecules given in the pair are the cis-trans isomers of the same molecule. To get the trans isomer from cis, rotation is needed around the double bond which is restricted. Hence the atoms in both molecules are not lined up perfectly, thus the given two molecules are nonsuperimposable.

Conclusion

All atoms of both molecules are not lined perfectly hence nonsuperimposable.

Interpretation Introduction

(d)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

The molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image, but not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are superimposable.

Explanation of Solution

Molecules in the given pair are:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  6

Two molecules given in pairs are the mirror images of each other. If one of the two given molecules is rotated around the central carbon atom it gives the exact similar molecule as another.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  7

Rotation of the molecule gives the molecule with a similar orientation as another molecule, thus two molecules are superimposable.

Conclusion

All atoms of both molecules are lined perfectly, hence superimposable.

Interpretation Introduction

(e)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

The molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image, but not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are superimposable.

Explanation of Solution

Molecules in the given pair are:

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  8

Both molecules in the given pair are isomers of the same molecules thus have the same attachments of the molecule with different orientations. Two chlorine atoms in the left molecule are pointing towards the observer while two chlorine atoms in the right molecule are pointing away from the observer. If one of the molecule rotates with 180o, it gives the molecule with a similar orientation as other.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  9

The molecule after the rotation of the left molecule has the exact similar orientation as the molecule at right, all atoms of both molecules are lined perfectly representing the molecules in the given pair are superimposable.

Conclusion

All atoms of both molecules are lined perfectly hence superimposable.

Interpretation Introduction

(f)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

Molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image, but not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are nonsuperimposable.

Explanation of Solution

Molecules in the given pair are

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  10

In the molecule at the left, both chlorine atoms are pointing towards the observer while in the molecule at right one chlorine atom is pointing towards the observer and one is pointing away from the observer. To get a similar orientation, rotation of the atom with the ring is needed which is restricted. Thus there is no orientation of both molecules lined perfectly, representing the molecules in the given pair are nonsuperimposable.

Conclusion

All atoms of both molecules are not lined perfectly, hence nonsuperimposable.

Interpretation Introduction

(g)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

Molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image. But not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are superimposable.

Explanation of Solution

Molecules in the given pair are

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  11

In the given pair both molecules are mirror images of each other having one chlorine atom pointing towards the observer and another pointing away from the observer.

The complete rotation of 180o of one molecule results from the molecule with the exact similar orientation of another molecule.

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  12

The molecule after the rotation of the left molecule has the exact similar orientation as the molecule at right, all atoms of both molecules are lined perfectly representing the molecules in the given pair are superimposable.

Conclusion

All atoms of both molecules are lined perfectly hence superimposable.

Interpretation Introduction

(h)

Interpretation:

Whether the molecules in the given pair are superimposable or nonsuperimposable is to be determined.

Concept introduction:

The molecules are nonsuperimposable if there is no orientation in which all atoms of both molecules can be lined up perfectly (i.e., superimposed). Every molecule can have a mirror image. But not every molecule can have a nonsuperimposable mirror image.

Expert Solution
Check Mark

Answer to Problem 5.1P

The given two molecules are nonsuperimposable.

Explanation of Solution

Molecules in the given pair are

Organic Chemistry: Principles and Mechanisms (Second Edition), Chapter 5, Problem 5.1P , additional homework tip  13

In the molecule at left both chlorine atoms are pointing towards the observer while in the molecule at right one chlorine atom is pointing towards the observer and one is pointing away from the observer. To get a similar orientation, rotation of the atom with the ring is needed which is restricted. Thus no orientation of both molecules lined perfectly, representing the molecules in the given pair are nonsuperimposable.

Conclusion

All atoms of both molecules are not lined perfectly hence nonsuperimposable.

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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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