Organic Chemistry, Ebook And Single-course Homework Access
Organic Chemistry, Ebook And Single-course Homework Access
6th Edition
ISBN: 9781319085841
Author: LOUDON
Publisher: MAC HIGHER
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Chapter 7, Problem 7.21P
Interpretation Introduction

(a)

Interpretation:

The difficulty of that would come on models of the cis and trans isomers of bicyclo[3.1.0]hexane made are to be stated. The model which will form easier is to be identified. The explanation for the corresponding answer is to be stated.

Concept introduction:

The organic compounds which consist of two cyclic rings fused together are known as bicyclic compounds. Fused rings, bridged rings, and spiro rings are the examples of bicyclic compounds. The stability of bicyclic compounds depends on the ring strain.

Expert Solution
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Answer to Problem 7.21P

The cis isomers of bicyclo[3.1.0]hexane will be formed with less difficulty than the trans isomers of bicyclo[3.1.0]hexane as the formation of three-membered cycles in a case where methyl group are at cis position to each other are easier than the trans position.

Explanation of Solution

The structure of cis and trans isomers of bicyclo[3.1.0]hexane are shown below.

Organic Chemistry, Ebook And Single-course Homework Access, Chapter 7, Problem 7.21P , additional homework tip  1

Figure 1

The formation of trans isomers of bicyclo[3.1.0]hexane is shown below.

Organic Chemistry, Ebook And Single-course Homework Access, Chapter 7, Problem 7.21P , additional homework tip  2

Figure 2

In the formation of trans isomers of bicyclo[3.1.0]hexane, the methyl groups are in two different planes. The angle between them is large. Therefore, it is difficult to form trans isomers of bicyclo[3.1.0]hexane.

The formation of cis isomers of bicyclo[3.1.0]hexane is shown below.

Organic Chemistry, Ebook And Single-course Homework Access, Chapter 7, Problem 7.21P , additional homework tip  3

Figure 3

In the formation of cis isomers of bicyclo[3.1.0]hexane, the methyl groups are in two same planes. The angle between them is not as large as in case of trans. Therefore, cis isomers of bicyclo[3.1.0]hexane will be form easier than the trans isomers of bicyclo[3.1.0]hexane.

Conclusion

It is easier to form a three-membered ring by the methyl at the cis position and the methyl groups at trans position. Therefore, cis isomers of bicyclo[3.1.0]hexane will form easier than the trans isomers of bicyclo[3.1.0]hexane.

Interpretation Introduction

(b)

Interpretation:

The difficulty of that would come on models of trans-bicyclo[3.1.0]hexane and trans-bicyclo[5.3.0]decane make is to be stated. The model which will form easier is to be identified. The explanation for the corresponding answer is to be stated.

Concept introduction:

The organic compounds which consist of two cyclic rings fused together are known as bicyclic compounds. Fused rings, bridged rings and spiro rings are the examples of bicyclic compounds. The stability of bicyclic compounds depends on the ring strain.

Expert Solution
Check Mark

Answer to Problem 7.21P

The compound trans-bicyclo[3.1.0]hexane will form with more difficulties than the compound trans-bicyclo[5.3.0]decane as the methyl groups in case of trans-bicyclo[3.1.0]hexane is movable than in case of formation trans-bicyclo[5.3.0]decane but rigid in case of trans-bicyclo[3.1.0]hexane.

Explanation of Solution

The structure of trans-bicyclo[3.1.0]hexane and trans-bicyclo[5.3.0]decane are shown below.

Organic Chemistry, Ebook And Single-course Homework Access, Chapter 7, Problem 7.21P , additional homework tip  4

Figure 4

The formation of trans-bicyclo[3.1.0]hexane is shown below.

Organic Chemistry, Ebook And Single-course Homework Access, Chapter 7, Problem 7.21P , additional homework tip  5

Figure 2

In the formation of trans-bicyclo[3.1.0]hexane, the methyl groups are in two different planes. The angle between them is large. Therefore, it is difficult to form trans isomers of bicyclo[3.1.0]hexane.

The formation of trans-bicyclo[5.3.0]decane is shown below.

Organic Chemistry, Ebook And Single-course Homework Access, Chapter 7, Problem 7.21P , additional homework tip  6

Figure 5

In the formation of trans-bicyclo[5.3.0]decane, the distance between methyl groups is not large. The angle between them can be change by sigma bond rotation. Therefore, it is easier to form trans-bicyclo[5.3.0]decane than trans-bicyclo[3.1.0]hexane.

Conclusion

The methyl groups in case of trans-bicyclo[3.1.0]hexane is movable than in case of formation trans-bicyclo[5.3.0]decane but rigid in case of trans-bicyclo[3.1.0]hexane. Therefore, compound trans-bicyclo[3.1.0]hexane will form with more difficulties than the compound trans-bicyclo[5.3.0]decane.

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