Meso compounds are achiral compounds that has multiple chiral centers. It is superimposed on its mirror image and is optically inactive despite its stereocenters. In general, a meso compound should contain two or more identical substituted stereocenters. Also, it has an internal symmetry plane that
divides the compound in half. These two halves reflect each other by the internal mirror. The stereochemistry of stereocenters should "cancel out". What it means here is that when we have an internal plane that splits the compound into two symmetrical sides, the stereochemistry of both left and right side should be opposite to each other, and therefore, result in optically inactive. Cyclic compounds may also be meso. If A is a meso compound, it should have two or more stereocenters, an internal plane, and the stereochemistry should be
R and S. trans-1,2-dichloro-1,2-ethanediol (meso)-2,3-dibromobutane Tips: An interesting thing about single bonds or sp3-orbitals is that we can rotate the substituted groups that attached to a stereocenter around to recognize the internal plane. As the molecule is rotated, its stereochemistry does not change. For example: Another case is when we rotate the whole molecule by 180 degree. Both molecules below are still meso. Remember the internal plane here is depicted on two dimensions. However, in reality, it is three dimensions, so be aware of it when we identify the internal mirror. Example This molecule has a plane of symmetry (the horizontal plane going through the red broken line) and, therefore, is achiral; However, it has two chiral carbons and is consequentially a meso compound. Example 2 This molecules has a plane of symmetry (the vertical plane going through the red broken line perpendicular to the plane of the ring) and, therefore, is achiral, but has has two chiral centers. Thus, its is a meso compound. Other Examples of meso compoundsMeso compounds can exist in many different forms such as pentane, butane, heptane, and even cyclobutane. They do not necessarily have to be two stereocenters, but can have more. Optical Activity AnalysisWhen the optical activity of a meso compound is attempted to be determined with a polarimeter, the indicator will not show (+) or (-). It simply means there is no certain direction of rotation of the polarized light, neither levorotatory (-) and dexorotatory (+). ProblemsBeside meso, there are also other types of molecules: enantiomer, diastereomer, and identical. Determine if the following molecules are meso. Answer key: A C, D, E are meso compounds. References
Which compounds are a meso compounds?Meso compounds can exist in many different forms such as pentane, butane, heptane, and even cyclobutane. They do not necessarily have to be two stereocenters, but can have more.
How do you find meso compounds?If there are two chiral centres and RS = SR, then it is a meso compound. Meso compound is optically inactive so the R cancels out S in a meso compound. Basically, if you can find out a plane of symmetry and two or more chiral centres in a compound then it is a meso compound.
Which of the following compounds are not meso?The trans isomer is not meso. Why? Simply because it is a chiral molecule! Do remember that the meso compound should have two or more tetrahedral chiral centers but still should be achiral!
How many isomers does a meso compound have?Achiral Diastereomers (meso-Compounds)
As a result, two of the four possible stereoisomers of this compound are identical due to a plane of symmetry, so there are only three stereoisomeric tartaric acids. Two of these stereoisomers are enantiomers and the third is an achiral diastereomer, called a meso compound.
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