Which of the following substituted cyclohexanes is most stable?

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Which of the following substituted cyclohexanes is most stable?

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E
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IV
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Transcribed Image Text:= E ***** IV V
Expert Solution
Step 1: Stability of cyclohexanes

The stability of cyclohexanes refers to the relative stability of different conformations of cyclohexane, a six-membered carbon ring.

The chair conformation is the most stable in cyclohexane because it minimizes ring strain by using a nearly ideal bond angle of roughly 109.5 degrees. The chair conformation allows for the most favorable orbital overlap and decreases steric interactions between substituents. The concept of ring strain and the effect of the substituents on the chair conformation of cyclohexane must be taken into account in order to assess the relative stability of the substituted cyclohexanes.

The given cyclohexanes are substituted with methyl groups which are shown as:

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