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Optical Isomers

Stereoisomers that are not geometric isomers are known as optical isomers. Optical isomers differ in the placement of substituted groups around one or more atoms of the molecule. They were given their name because of their interactions with plane-polarized light. Optical isomers are labeled enantiomers or diastereomers.

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Enantiomers are non-superimposable mirror images. A common example of a pair of enantiomers is your hands. Your hands are mirror images of one another but no matter how you turn, twist, or rotate your hands, they are not superimposable.

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Figure (PageIndex{5}): Two models that are mirror images and superimposable. Since they are superimposable, they are the same molecule and are not isomers.

Figure (PageIndex{6}): Your hands and some molecules are mirror images but are not superimposable. These pairs of molecules are called enantiomers.

Objects that have non-superimposable mirror images are called chiral. When examining a molecule, carbon atoms with four unique groups attached are considered chiral. Look at the figure below to see an example of a chiral molecule. Note that we have to look beyond the first atom attached to the central carbon atom. The four circles indicate the four unique groups attached to the central carbon atom, which is chiral.

Figure (PageIndex{7}): A chiral carbon has four unique groups attached to it.

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Another type of optical isomer are diastereomers, which are non-mirror image optical isomers. Diastereomers have a different arrangement around one or more atoms while some of the atoms have the same arrangement. As shown in the figure below, note that the orientation of groups on the first and third carbons are different but the second one remains the same so they are not the same molecule. The solid wedge indicates a group coming out of the page/screen towards you and the dashed line indicates that a group is going away from you “behind” the page/screen.

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Figure (PageIndex{8}): Diastereomers differ at one or more atom. These molecules are not mirror images and they are not superimposable. They are optical isomers because they have the same connectivity between atoms but a different arrangement of substituent groups.

Epimers are a sub-group of diastereomers that differ at only one location. All epimers are diastereomers but not all diastereomers are epimers.

Figure (PageIndex{9}): Epimers have a different arrangement around one atom, while arrangements around the other atoms are the same.

Figure (PageIndex{10}): Diagram showing the division of stereoisomers (also known as optical isomers).

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