Problem: The all-trans-1,2,3,4,5,6-hexaethylcyclohexane ( 1) prefers the all-equatorial conformation while the all-trans-1,2,3,4,5,6-hexaisopropylcyclohexane (2) possesses a severely destabilized all-equatorial conformation (J. Am. Chem. Soc. 1990, 112, 893–894): (a) By examining a molecular model of cyclohexane with several all  trans-equatorial isopropyl groups and another model with several all-trans-equatorial ethyl groups, determine why adjacent equatorially oriented isopropyl groups experience severe steric interactions which are lacking in the ethyl case. Draw a chair conformation of the former case which illustrates these severe steric interactions. Also draw a Newman projection looking down one of the C—C bonds connecting the cyclohexyl ring to an equatorial isopropyl group and illustrate a conformation with severe steric strain.  

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The all-trans-1,2,3,4,5,6-hexaethylcyclohexane ( 1) prefers the all-equatorial conformation while the all-trans-1,2,3,4,5,6-hexaisopropylcyclohexane (2) possesses a severely destabilized all-equatorial conformation (J. Am. Chem. Soc. 1990, 112, 893–894):

(a) By examining a molecular model of cyclohexane with several all  trans-equatorial isopropyl groups and another model with several all-trans-equatorial ethyl groups, determine why adjacent equatorially oriented isopropyl groups experience severe steric interactions which are lacking in the ethyl case. Draw a chair conformation of the former case which illustrates these severe steric interactions. Also draw a Newman projection looking down one of the C—C bonds connecting the cyclohexyl ring to an equatorial isopropyl group and illustrate a conformation with severe steric strain.

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Our data indicates that this problem or a close variation was asked in Organic Chemistry - Klein 2nd Edition. You can also practice Organic Chemistry - Klein 2nd Edition practice problems.