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Introductory Chemistry: A Foundation

9th Edition

ISBN:9781337399425

Author:Steven S. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Donald J. DeCoste

Chapter3: Matter

Section: Chapter Questions

Problem 1QAP

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Question

Draw both chair confirmations of the substituted cyclohexane drawn below. Be certain to actually do a ring flip. Also be certain to very clearly distinguish axial from equatorial positions. Then circle the more stable conformation. Draw a planar representation of a stereoisomers which would have a higher heat of combustion and lower heat of combustion.

Expert Solution

Step 1

The given compound, (1S,2S,4R)-1-isopropyl-2,4-dimethylcyclohexane is in planar form. It contains two methyl groups and one isopropyl group. The isopropyl group is bulkier than methyl group, therefore to avoid the 1,3-diaxial repulsion, isopropyl group will prefer to stay at equatorial position in stable form.

Step 2

The given below chair forms depicts the more stable form of given compound by considering the flipping.

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