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Organic Chemistry 4e Carey | |||||
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Substituted Cyclohexanes |
Chapter 3: Conformations of Alkanes and Cycloalkanes |
In order to view some of the structures for this section, you will need the web "plug-in", "CHIME". If you do not have it already installed, you should be able to download it for free from the linked Website. CHIME is a browser that allows you to visualize and manipulate molecules as 3D structures. Check here if you don't know how to use Chime.
Substituents on cyclohexane can, in principle, occupy either axial or equatorial positions. However, in general, equatorial substituents are more preferred since they are more stable because of reduced steric interactions.
This is shown in the following
example for methycyclohexane.
In the equatorial system, the methyl group is anti to the C-C bonds in
the rest of the ring system. However, in the axial conformation, a steric
interaction of the methyl group with the two axial hydrogen atoms on the same
face of the ring destabilizes the axial conformation. In the images below, this
1,3-diaxial interaction can be highlighted and contrasted with
the equatorial conformer. The effect is most obvious when viewed in the spacefilling
model.
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Click here to reset colors |
Click here to highlight 1,3-diaxial hydrogen atoms Click here to reset colors |
The larger the alkyl substituent is, the greater the preference for the equatorial position since the larger the group the greater the steric interaction with the axial hydrogens.