Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 7, Problem 7.1P
Interpretation Introduction

Interpretation:

A model of chair cyclohexane corresponding to the leftmost model in the given figure is to be drawn. The two reasons corresponding to the fact that the half-chair conformation is less stable than the chair or twist-boat conformation is to be stated.

Concept introduction:

The conformation of cyclohexane is a type of 3D shape of cyclohexane molecule. There are total four types of significant conformations of cyclohexane exists which are chair conformation, half-chair conformation, boat conformation and twist-boat conformation. The switching of cyclohexane molecule is very easy between the four conformations.

Expert Solution & Answer
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Answer to Problem 7.1P

A model of chair cyclohexane corresponding to the leftmost model in the given figure is shown below.

Organic Chemistry, Chapter 7, Problem 7.1P , additional homework tip  1

The half-chair conformation is less stable than the chair or twist-boat conformation because half-chair conformation has maximum ring strain and the presence of angle strain in half-chair conformation of cyclohexane molecule.

Explanation of Solution

The given leftmost figure of chair conformation of cyclohexane is shown as,

Organic Chemistry, Chapter 7, Problem 7.1P , additional homework tip  2

Figure 1

The model of chair conformation of cyclohexane corresponding to the leftmost model is shown as,

Organic Chemistry, Chapter 7, Problem 7.1P , additional homework tip  3

Figure 2

If the carbon-4 in order to locate carbons 2-5 in a common plane then the above model chair conformation of cyclohexane is shown as,

Organic Chemistry, Chapter 7, Problem 7.1P , additional homework tip  4

Figure 3

Thus, the raising of carbon-4 in order to locate carbons 2-5 in a common plane forms the half-chair conformation of cyclohexane molecule. This half-chair conformation of cyclohexane molecule is a transition state for the conversion into the chair and twist boat conformations.

The two reasons which explain that the half-chair conformation is less stable than the chair or twist-boat conformation are as follows.

• The ring strain in half chair conformation is more as compared to the chair or twist-boat conformation.

• The angle strain of 120° and torsional strain is present in half chair conformation of cyclohexane. These two strains exist in the half chair conformation because of the two fully eclipsed carbon-carbon bonds and two partially eclipsed carbon-carbon bonds.

Conclusion

A model of chair cyclohexane corresponding to the leftmost model in the given figure has been shown above. The two reasons corresponding to the fact that the half-chair conformation is less stable than the chair or twist-boat conformations has been stated above.

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