Cycloalkane rings with a size of 7 and fewer cannot be turned inside-out without breaking C-C bonds. One consequence of this is "geometric isomerism" : two groups on the same side of a small cycloalkane ("cis") are locked in position, as are two groups on opposite sides ("trans"). cis- and trans- isomers have different physical properties and cannot be interconverted through bond rotation.
Here, models of cycloalkane rings of various sizes (3-9) with two cis substituents (denoted in red) are rotated to show how increasing the ring size increases the degrees of freedom in the cycloalkane.
