Cyclopropane

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4-7-2019

1821

Cyclopropane is always at maximum torsional strain. This strain can be illustrated in a line drawing of cyclopropane as shown from the side. In this oblique view, the dark lines mean that those sides of the ring are closer to you.

However, the ring isn't big enough to introduce any steric strain, which does not become a factor until we reach six membered rings. Until that point, rings are not flexible enough for two atoms to reach around and bump into each other.

The really big problem with cyclopropane is that the C-C-C bond angles are all too small.

• All the carbon atoms in cyclopropane appear to be tetrahedral.
• These bond angles ought to be 109 degrees.
• The angles in an equilateral triangle are actually 60 degrees, about half as large as the optimum angle.
• This factor introduces a huge amount of strain in the molecule, called ring strain.