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Chapter 4: 4-20 (page 112)

Which isomer is more stable, cis-decalin or trans-decalin? Explain.

Short Answer

Expert verified

Trans-decalin is more stable as it shows fewer steric interactions.

Step by step solution

01

Cis and trans conformation of decalin

In cis-decalin, the hydrogen atoms at the bridgehead carbons are on the same face of the rings; in trans-decalin, the bridgehead hydrogens are on opposite faces.

02

Axial and equatorial positions

Axial bonds are the bonds that are perpendicular or vertical to the ring plane. Equatorial bonds are approximately horizontal in the plane of the ring.

03

Conformation stability

Cis- and trans-decalin, respectively

Trans-decalin is more stable than cis-decalin because the rings are at a maximum distance in trans-decalin, and in cis-decalin show steric interactions and hence, decreases its stability.

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Most popular questions from this chapter

Draw structures corresponding to the following IUPAC names:

a) 1,1 dimethyl cyclooctane

b) 3-cyclobutyl hexane

c) 1,2 -dichloro cyclopentane

d) 1,2- dibromo, 5- methylcyclohexane

A 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.

Draw the two chair conformations of cis-1-chloro-2-methylcyclohexane. Which is more stable, and by how much?

The following cyclohexane derivative has three red, green, and blue substituents. Identify each substituent as axial or equatorial, and identify each pair of relationships (red鈥揵lue, red-green, and blue-green) as cis or trans.

Why is a 1, 3-cis disubstituted cyclohexane more stable than its trans isomer?
See all solutions

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