November 27, 2024, 06:45:48 PM
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Topic: Why is the trans-1,3-di-tert-butylcyclohexane more stable in twist-boat?  (Read 2253 times)

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Offline windom626

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Im just trying to get this right, so i draw the trans-1,3-di-tert-butylcyclohexane in a chair conformation, and i counted the energies of steric strains, correct me if im wrong, are there 4, 1,3 diaxial interactions? Which would give us a total of 45,6 kJ/mol to keep this structure stable, and in the twist-boat conformation there are only 3 of those interactions? And that's why it is more stable? Am i geting this correct?


Offline rolnor

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This is a very good example were you can do some molecular modeling. I don know if you are right though, very possible. I have used ”PC-Model” from Serena Software, very useful in cases like this.

Offline hollytara

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t-butyl in axial position is very disfavored by energy.  When you have trans 1,3 - both chairs have 1 axial and 1 equatorial, so both chairs are disfavored.  Twist boat can minimize the unfavorable interactions from the t-butyls and this makes it more favorable in this case. 

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