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6.6 Comparing the Stability of Chairs
If you have drawn both chair conformations for a substituted cyclohexane, you should be able to predict which one is more stable.
This is where reactivity gets important.
Imagine that you are learning about a reaction that can only happen if a certain group is in a certain position.
You already know that the groups are flipping between the two positions, as it goes back and forth from one chair to the other.
The reaction can't happen if it's equatorial.
The reaction would be very slow because it could only happen during 1% of the time when the group is in the axial position.
The reaction will happen very quickly if the group is in an axis 99% of the time.
It's important to understand what makes a chair unstable.
The bigger the group, the better it will be.
The butyl group will spend most of its time in an equator.
The ring in the chair will be locked if this is done.
This effect will speed up the reaction if we are trying to run it in a way that is axial.
Let's take a step by step approach in determining which chair is more stable.
If the ring has more than two groups, you can use the same logic that we used to choose the more stable chair.
Put the largest groups in the middle of the jungle.
The chair with the larger group in the equatorial position was selected.
Draw the most stable chair conformation for each compound.
It is worth a couple of paragraphs to clear up some confusing terminology.
There aren't double bonds here.
Don't draw double bonds.
The ending means that there are no double bonds in the molecule.
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