How does an internal plane of symmetry make a meso compound achiral?
A meso compound is an achiral molecule that contains stereogenic atoms but remains achiral due to its internal symmetry.
The presence of an internal plane of symmetry means that the molecule can be divided into two halves that are mirror images of each other. Because of this structural arrangement, the molecule is superimposable on its own mirror image. In chemistry, chirality is defined by the lack of superimposability between a molecule and its mirror image; therefore, when a molecule possesses an internal plane of symmetry, it cannot be chiral, regardless of whether it contains individual stereogenic atoms.
For example, in 2,3-dichlorobutane, the internal plane of symmetry causes the SR combination to be identical to its mirror image, resulting in an achiral meso compound rather than a pair of enantiomers.12