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Stereoisomers are molecules with the same formula and connectivity but different arrangement

of their atoms in space.

A molecule is chiral if it cannot be superimposed on its mirror image (which is called its
“enantiomer”).

The word “chiral” refers to any object that cannot be directly superimposed on its mirror image.
These molecules lack symmetry, which makes it possible for this to happen.

The word “chiral” refers to any object that cannot be directly superimposed on its mirror image.
These molecules lack symmetry, which makes it possible for this to happen.

Enantiomers are stereoisomers that are related to each other as being nonsuperimposable mirror
images.

The R stands for the Latin word rectus and the S stands for the Latin word sinister. Rectus
means “right” and sinister means “left.”

The system we use to name chiral molecules is the R/S naming system. In this naming system,
we assign a ranking to each of the substituents on a stereocenter and see if their order is
arranged in a clockwise or counterclockwise fashion, when the molecule is oriented just so.
Stereocenters that have a clockwise order are referred to as R, and stereocenters that have a
counterclockwise order are referred to as S.

 Rank the substituents using the same rules that were used for E/Z isomerism. The
highest-priority group is given the number 1, followed by (straightforwardly enough) 2, 3,
and 4.
 Draw the molecule (or even better, use a model) so that the lowest-priority group is
pointing away from you.
 Draw an arrow from the highest-priority group (1) to the next highest (2) and then to the
third highest (3).
 If the arrow points clockwise, the configuration is R. If it points counterclockwise, the
configuration is S.
 Name the molecule by putting the letter before the name of the molecule in parentheses.

The highest-priority substituent is the “–OH” group because oxygen has a higher priority than
carbon, so number it with a “1.” The next highest-priority substituent is the “–CO 2H” group
(label it “2”) and the third highest-priority substituent is “–CH3” (label it “3”). Finally, lowly
hydrogen is given lowest priority (label it “4”). When we point the molecule so that hydrogen
faces away from us, it should be clear that this is the R form of lactic acid:

Diastereomers are stereoisomers that are not mirror images of one another.
A meso compound or meso isomer is a stereoisomer with an identical or superimposable
mirror image i.e., a non-optically active member of a set of stereoisomers, at least two of which
are optically active. This means that despite containing two or more stereogenic centers, the
molecule is not chiral. A meso compound is "superposable" on its mirror image (not to be
confused with superimposable, as any two objects can be superimposed over one another
regardless of whether they are the same). Two objects can be superposed if all aspects of the
objects coincide) and it does not produce a "(+)" or "(-)" reading when analyzed with
a polarimeter.

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