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Following is a planar hexagon representation for one isomer of

Chapter 2, Problem 2.13

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QUESTION:

Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcy-clohexane. Draw the alternative chair conformations of this compound and statewhich of the two is more stable.

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QUESTION:

Following is a planar hexagon representation for one isomer of 1,2,4-trimethylcy-clohexane. Draw the alternative chair conformations of this compound and statewhich of the two is more stable.

ANSWER:

Key concepts

Chair conformation

The most stable conformation of a cyclohexane ring; all bond angles are close to 109.5°, and all bonds on adjacent carbons are staggered.

Diaxial interaction

Diaxial interaction refers to the steric strain arising from interaction between an axial substituent and an axial hydrogen (or another group) on the same side of a chair conformation of a cyclohexane ring.

Step 1 of 4

We are given a planar hexagon representation for one isomer of 1,2,4-trimethylcyclohexane.

Now we have to draw the alternative chair conformations of this compound and state which of the two is more stable.

To draw an alternate chair conformation, one must first convert to the boat confirmation then back to an alternate form of the chair conformation.

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