Organic Chemistry

Learn the toughest concepts covered in Organic Chemistry with step-by-step video tutorials and practice problems by world-class tutors.

4. Alkanes and Cycloalkanes

Equatorial Preference

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This is the #1 thing you need to know about cyclohexane. So let’s get right into it.

Determining the Best Position

1

concept

Equatorial Preference

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  • Blue = Axial. This position sucks, it’s really cramped up. Large groups can’t stand it.
  • Green = Equatorial. This position is awesome. Large groups want to flip to this position

Determining Equatorial Preference

We always want to draw our chairs with the largest groups equatorial. If they are axial, we need to flip the chair. 

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example

Draw the following chair in the most stable conformation.

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Don’t worry about drawing this problem out correctly on the first try, as long as you know how to flip it to the correct chair, that’s all that matters. 

3
Problem

Draw the MOST STABLE conformation of cis-1-tert-butyl-4-methylcyclohexane.

Hint: If you don’t know what neopentyl is, it’s ok. Obviously it has 5 carbons, so keep that in mind when deciding equatorial preference!

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Problem

Draw the LEAST STABLE conformation of trans-1-tert-butyl-3-neopentylcyclohexane.