Organic Chemistry
Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 7, Problem 7.40AP
Interpretation Introduction

Interpretation:

The reason as to why the energy difference of the two chair forms of methylcyclohexane and ethylcyclohexane is same is to be stated.

Concept introduction:

The saturated six membered ring compounds are mostly expressed and explained in the chair conformations. This is because chair conformation is the most stable conformation of cyclohexane. Therefore, the chair conformation is most helpful in the studies of six carbon ring compounds.

There are forms of chair conformation one is axial form if the substituent is at axial position and other is equatorial form if the substituent is at equatorial position.

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Is there a difference in the stability of the two cyclohexane conformations?
Given cyclohexane in a chair conformation, construct the more stable conformation of cis‑1‑methyl‑2‑propylcyclohexane by filling in the missing atoms or groups. Use the numbering provided on the ring.
The energy difference between a tert-butyl group going from equatorial to axial in a cyclohexane is 18.3 kJ/mol. When two of the carbon atoms are replaced with oxygen atoms (molecule B) the energy difference between the two chair conformations drops to 5.9 kJ/mol. Explain this difference. (Hint: Consider what makes putting groups axial unfavorable).

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