A slightly easier method to determine whether a given compound is meso is to take advantage of a simple principle: meso compounds have an internal mirror plane. Meso Compounds. Organic chemistry 15: Stereochemistry - meso compounds, resolution. The chiral centers should have four unique substituents. Meso compounds are compounds that have an internal mirror plane, or a plane of symmetry, and at least two chiral centers. What is a meso compound? Meso Compounds What is a Meso Compound? However, that mirror image is also the compound itself. Meso compounds In the simplest case, a compound with two chirality centers where there is the same set of four groups at each chirality center, the combination where the four groups are arranged such that the centers are mirror images of each other ( i.e. Like any other molecule that is not chiral, meso compounds cannot have enantiomers since their mirror image represents the same compound: Wedge and dash in Meso compounds. Meso compounds are molecules that have multiple stereocenters but are superimposable on their mirror images. where the molecule has an internal mirror plane) is a meso compound. Meso compounds do not have an enantiomer but do have a plane of symmetry. 2) Meso compounds cannot have enantiomers. Because the mirror image is the compound itself, it is not considered to have an enantiomer of itself. A meso compound does have a mirror image of itself and it does have chirality centers. Meso compounds are achiral molecules that possess multiple chiral centres.The reason for them being achiral is because they possess an internal plane of symmetry (also known as centre of symmetry). Mar 6, 2015 • ericminikel • Cambridge, MA • chem-20 These are my notes from lecture 15 of Harvard’s Chemistry 20: Organic Chemistry course, delivered by Dr. Ryan Spoering on March 6, 2015. This is because meso compounds contain an internal plane of symmetry; the molecule can be split by an imaginary mirror so that all atoms on one side of the mirror … For the given six member rings, the key to identifying the meso compound is finding the structure in which the two chlorine atoms are on the same side of the ring. A meso compound contains at least two stereogenic centers, yet the molecule itself is not chiral. Q: Why should we care about them in our organic chemistry class? Meso compounds are characterized by an internal plane of symmetry that renders them achiral despite the presence of chiral center(s). A diastereomer of a meso compound is a different compound. We care because this is an easy place for a professor to try to trip you up. (2 R ,3 S )- Tartaric acid is a meso compound. Illustrated Glossary of Organic Chemistry Meso (meso compound): An achiral substance that also has two or more stereocenters . Also, the stereochemistry of the compound should be R and S. Fischer projections are used to identify the configuration of a compound and the configurational relationships that are present in the isomers of the compound. A meso compound is a molecule with multiple stereocenters that is superimposable on its mirror image. For identification of a meso compound, it should possess atleast two stereocenters and an internal plane to bisect the compound. Sometimes, it is not obvious to spot the meso isomer when it is drawn in bond-line representation.