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Ring Strain in Cycloalkanes

By German Fernandez, 26 May, 2024

Ring Strain in Cyclopropane

As can be observed in the molecular model, cyclopropane has bond angles of 60º, which is a significant deviation from the typical 109.5º of sp3 carbons. Additionally, the hydrogens are eclipsed, three on the upper face and three on the lower face. These two factors, angular strain and eclipsing, make cyclopropane a high-energy molecule.
Cyclopropane is planar and has no mechanism to relieve this strain. In other cycloalkanes, spatial arrangements help minimize hydrogen-hydrogen eclipsing interactions.

Cyclopropane is a planar molecule with significant strain due to small bond angles and hydrogen interactions

Ring Strain in Cyclobutane

Cyclobutane has bond angles of 90º between carbons, causing significant strain, though much less than that in cyclopropane. In its planar form, it has four eclipsed hydrogens on each face. Cyclobutane reduces eclipsing by moving the opposite carbons out of the plane.

Cyclobutane avoids much of the hydrogen repulsion by moving two carbon atoms out of the plane

Ring Strain in Cyclopentane

The bond angles in cyclopentane are very close to 109º, making this molecule nearly free of angular strain. It has five hydrogen-hydrogen eclipsing interactions on each face, which it minimizes by adopting a spatial arrangement called the envelope form.

Cyclopentane is not a planar molecule; it adopts an envelope conformation that minimizes hydrogen repulsions

 

Book traversal links for Tensión Anular en Cicloalcanos

  • Cycloalkanes nomenclature
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  • Cyclopropane Structure

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