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For each of the following pairs of compounds, determine

Chapter 4, Problem 4.55

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QUESTION:

For each of the following pairs of compounds, determine which compound is more stable (you may find it helpful to draw out the chair conformations): (a) (b) (c) (d)

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QUESTION:

For each of the following pairs of compounds, determine which compound is more stable (you may find it helpful to draw out the chair conformations): (a) (b) (c) (d)

ANSWER:

Step 1 of 4

a.  To draw these compounds in chair conformations, number the carbons if needed to keep track of the substituents. Below are the lowest energy chair conformations for each compound.

 

     

It can be seen that the let compound cannot assume a chair conformation with all substituents in equatorial positions like the right compound, so the compound on the right is more stable.

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