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Anonymous asked in Science & MathematicsChemistry · 1 decade ago

Why is cis-1,3-dimethylcyclobutane more stable than trans-1,3-dimethylcyclobutane?

My textbook ( Organic Chemistry by Mr. Wade ) says that and I don't understande.

The less repulsion a molecule has, the more stable it is. Why not for this case?

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  • 1 decade ago
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    It is because cyclobutane looks like a square piece of paper with a fold along the diagonal. If you add the methyl groups to the corners not on the fold, they can be both axial or both equatorial. The axial is the less stable conformation than diequatorial. If it is the trans compound, then it will have one axial and one equatorial. Just as two equatorial groups are more stable, only one equatorial group will be less stable.

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  • 4 years ago

    This isnt a concrete answer yet purely greater o f a guideline yet i understand with cyclohexane they may well be cis yet are greater solid by way of fact they might the two be equatorial and consequently finally extra different than for one yet another.

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