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7.4.3–7.4.5 Diastereomers

7.4.3 Compounds with 2 or more stereocenters

Let’s look at all of the possible stereoisomers of 2-bromo-3-chlorobutane and how they are related to each other. Two of the stereoisomers, (2S,3R) and (2R,3S) are enantiomers. They are non-identical mirror images of each other. (2R,3R) and (2S,3S) are also enantiomers. They are non-identical mirror images of each other.

Compounds with 2 or more stereocenters

But, how are (2R,3S) and (2R,3R) related to each other? They are stereoisomers of each other, but they are not mirror images of each other. There is a name for this relationship. They are diastereomers of each other. Diastereomers are stereoisomers that are not mirror images of each other.

Enantiomers and Diastereomers
Enantiomers and Diastereomers

7.4.4 Other examples of diastereomers

Geometric isomers, also called cis-trans isomers, are another example of diastereomers. They are stereoisomers that are not mirror images of each other.

Geometric isomers are also diastereomers
Geometric isomers are also diastereomers

7. Label the following compounds as enantiomers, diastereomers, the same compound, or neither.

a)
Problem 7a, diastereomers
b)
Problem 7b, diastereomers
c)
Problem 7c, diastereomers
d)
Problem 7d, diastereomers
Problem 7d, diastereomers, answer

7.4.5 Meso Compounds

Compounds that have stereogenic atoms but are achiral are called meso compounds. These compounds typically have stereogenic atoms, but they have a mirror plane of symmetry to prevent them from becoming chiral.

Meso vs. enantioimeric pair
Meso vs. enantioimeric pair

8. Circle each of the following compounds that is a meso compound.

Problem 8, diastereomers (1 of 4)
Problem 8, diastereomers (2 of 4)
Problem 8, diastereomers (3 of 4)
Problem 8, diastereomers (4 of 4)
Problem 8, diastereomers, answer