Monosubstituted cyclohexanes occur in two equilibrium conformations. In oneconformation, the substituent is in an axial position. In the other conformation, the substituentis in the equatorial position. Complete the drawing of each chair conformation below and circlethe more stable conformation.

Answered: Monosubstituted cyclohexanes occur in…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter7: Cycloalkanes

Section: Chapter Questions

Problem 12CTQ: Fill in the blanks: cis-1,3-Dimethylcyclohexane has two different chair conformations: one withboth...

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Monosubstituted cyclohexanes occur in two equilibrium conformations. In one
conformation, the substituent is in an axial position. In the other conformation, the substituent
is in the equatorial position. Complete the drawing of each chair conformation below and circle
the more stable conformation.

Expert Solution

Step 1

The most stable conformation having methyl group is at equatorial position.

Methy group at axial position create steric hinderance Or create butane gauch interaction with C2-C3 and C6-C5 bond or diaxial interactions with C3 and C5 axial Hydrogen atom (as shown in below image) due to this interaction the energy of axial conformation increases and conformation is less stable.

Methy group at equatorial position does not craete such any interaction so energy of conformation goes down and conformation become more stable.

So equatorial methyl group conformation is more stable than axial methyl group conformation.

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