In organic chemistry, what is a meso compound?

A meso compound is characterized by having multiple stereocenters and an internal plane of symmetry. This symmetry allows the molecule to be superimposable on its mirror image, meaning it is achiral, despite containing chiral centers.

In the context of meso compounds, the presence of multiple stereocenters often generates the potential for stereoisomers, but the internal plane of symmetry cancels out their optical activity. This is crucial for recognizing meso compounds—while they may contain stereogenic centers that typically would confer chirality, their symmetrical structure results in an overall non-chiral molecule.

Therefore, the defining feature of a meso compound lies in its composition of stereocenters and the specific arrangement that leads to symmetry, allowing it to demonstrate unique chemical properties and implications in stereochemistry.