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Meso Compounds

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    799
  • [ "article:topic", "Lower Division", "Meso Compounds", "showtoc:no" ]

    Meso compounds are achiral compounds that has multiple chiral centers. It is superimposed on its mirror image and is optically inactive despite its stereocenters.

    Introduction

    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.

    Identification

    If A is a meso compound, it should have two or more stereocenters, an internal plane, and the stereochemistry should be R and S.

    1. Look for an internal plane, or internal mirror, that lies in between the compound.
    2. The stereochemistry (e.g. R or S) is very crucial in determining whether it is a meso compound or not. As mentioned above, a meso compound is optically inactive, so their stereochemistry should cancel out. For instance, R cancels S out in a meso compound with two stereocenters.

           Meso1 (1).bmp

    trans-1,2-dichloro-1,2-ethanediol

    Meso2 (5).bmp

    (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:

                 rotated (1).bmp

    Another case is when we rotate the whole molecule by 180 degree. Both molecules below are still meso.

    rotated180.bmp

    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 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.

     

    Meso3 (1).bmp

    Cyclic.bmp

    Optical Activity Analysis

    When 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 (+).

    Problems

    Beside meso, there are also other types of molecules: enantiomer, diastereomer, and identical. Determine if the following molecules are meso.

    Mesopracticeprob.bmp

    Answer key: A C, D, E are meso compounds.

    References

    1. Vollhardt, K. P.C. & Shore, N. (2007). Organic Chemistry (5thEd.).  New York: W. H. Freeman. (190-192)
    2. Shore, N. (2007). Study Guide and Solutions Manual for Organic Chemistry (5th Ed.). New York: W.H. Freeman. (70-80)

    Contributors

    • Duy Dang