Textbook Question
Predict which side of the equilibrium is favored for each of the chair–chair interconversions (ring flips) shown.
(c)
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4. Alkanes and Cycloalkanes
Equatorial Preference
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Draw the LEAST STABLE conformation of trans-1-tert-butyl-3-neopentylcyclohexane.
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Verified step by step guidance1
Identify the structure of trans-1-tert-butyl-3-neopentylcyclohexane. The 'trans' configuration means that the two substituents are on opposite sides of the cyclohexane ring.
Understand that cyclohexane can adopt different conformations, with the chair conformation being the most stable. However, we are looking for the least stable conformation.
In the chair conformation, substituents can be in axial or equatorial positions. Axial positions are less stable due to 1,3-diaxial interactions, especially with bulky groups.
Place the tert-butyl group in an axial position. This is a large group, and placing it axially will create significant steric strain, contributing to instability.
Place the neopentyl group in an axial position on the opposite side of the ring. This will further increase steric strain and make the conformation less stable.
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