Symmetry Planes and Stereoisomers

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Molecules with the same molecular formula but a different spatial arrangement are classified as stereoisomers. These can be either enantiomers or diastereomers. Two molecules are called enantiomers if they are mirror images. They are diastereomers if no plane of reflection exists. Diastereomers can have different physical properties and reactivities. In this Demonstration, the molecules considered have two chiral centers (), thus the maximum number of stereoisomers is equal to 4 (), or 3 if the two chiral centers are identical. A meso form has two chiral centers but is superposable with its mirror image and thus optically inactive.


Select the different cases using the "stereoisomers" buttons. The two chiral centers correspond to carbon atoms with different substituents; the substituents responsible for the structure are:


Use the "reflected molecule rotation" slider to rotate the mirror image of the molecule. If you do not want the meso compound, change a substituent in a chiral center using the "different substitution" checkbox, which eliminates the plane of symmetry.


Contributed by: D. Meliga, A. Ratti, L. Lavagnino and S. Z. Lavagnino (August 2022)
Open content licensed under CC BY-NC-SA



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