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Question

Which of the following cycloalkanes involves maximum torsional strain?


A

Cyclopropane

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B

Cyclobutane

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C

Cyclopentane

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D

Cyclohexane

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Solution

The correct option is A

Cyclopropane


From the given compounds, all of them are cycloalkanes with the carbons supposedly having sp3 hybridizations as per VSEPR. But because they are all cyclic, the bond angles at the ring carbons will not be exactly equal to 109 28.

According to Baeyer’s strain theory, the amount of the strain is directly proportional to the angle of deviation. Angle of deviation, d = 12(109 28'- valency angle). d is maximum in case of cyclopropane, thus torsional strain is maximum in cyclopropane.


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