Propane

Similar to ethane, the propane staggered conformation is more stable than the eclipsed
and the CH3 groups are capable of undergoing rotation. In ethane, the barrier to this
rotation (i.e., the difference in energy between the staggered and eclipsed
conformations) is 2.8 kcal/mol, however in propane; this barrier is 3.2 kcal/mol. This
increase in energy is due to the greater steric interaction between a methyl group and
hydrogen; in ethane, the eclipsed conformation contains three H & H eclipsing
interaction, however, the eclipsed conformation of propane has two H & H eclipsing
interactions and one H & CH3 eclipsing interaction. The 0.4 kcal/mol increase in
energy is due to the greater size of the methyl group, which repels the H to a greater
extent. Thus, with molecular interactions, size matters, and the larger the groups, the
more severe the interaction. As such, each H & H interaction is worth about 0.9
kcal/mol, and each H – CH3 interaction is worth about 1.3 kcal/mol.

Cyclopentane has very little angle strain (the angles of a pentagon are 108º), but its
eclipsing strain would be large (about 10 K.cal/mol) if it remained planar.
Consequently, the five-membered ring adopts non-planar puckered (or) envelop
structure conformations whenever possible. Rings larger than cyclopentane would
have angle strain if they were planar. However, this strain, together with the eclipsing
strain inherent in a planar structure, can be relieved by envelop structure (or)
puckering the ring.