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Description of Diastereomers

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Diastereomers

Diastereomers are a type of a stereoisomer, which are not mirror images of one another and are non-superimposable on one another. Diastereomers occurs when two or more stereoisomers of a compound have different configurations at one or more (but not all) of the equivalent stereocenters and are not mirror images of each other.

Diastereomers that contains more than one chiral center but different from each other in the absolute configuration   at only one chiral center is  called epimers. Each stereocenter gives rise to two different configurations and thus typically increases the number of stereoisomers by a factor of two. An example of epimer is shown in figure: a.

Figure: a

Enantiomers 

Enantiomers are chiral molecules that are mirror images of one another. Furthermore, the molecules are non-superimposable on one another. This means that the molecules cannot be placed on top of one another and give the same molecule. Chiral molecules with one or more stereocenters can be enantiomers. The example of enantiomer is hown below in Figure: b.

Figure: b

Solved examples of Diastereomers

Example 1: Consider the following pairs of molecules and determine whether they are diastereomers or not?

 

Figure: 1.0

Solution: These molecules are diastereomers. These molecules are not mirror images of one another, and they are non-superimposable, which can be seen by flipping one of the molecules 180 degrees, as shown below in Figure: 1.0 (a). The stereochemistry is the same at the stereocenter attached to the methyl group and is different at the other stereocenter attached to the chlorine. 

 

Figure: 1.0 (a)

Example 2: Consider the following pairs of molecules and determine whether they are diastereomers or not?

Figure: 2.0

Solution: These molecules are not mirror images of one another. Additionally, these molecules are non-superimposable because if one of these molecules is flipped 180 degree, so that the alcohols and methyls are aligned, as shown below in Figure: 2.0 (a), the stereochemistry is different at one carbon (the alcohols) and the same at another carbon (the methyls). Therefore, these molecules are diastereomers. 

Figure: 2.0 (a)

Example 3: Consider the following pairs of molecules and determine whether they are diastereomers or not?

Figure: 3.0

Solution: These molecules are not diastereomers. These molecules are non-superimposable, which can be seen by flipping one of the molecules 180 degrees, as shown below in Figure: 3.0(a). In one molecule, the alcohol and chlorine are wedged and the methyl is dashed, and in the other molecule, the alcohol and chlorine are dashed and the methyl is wedged. However, these molecules are mirror images of one another. Therefore, these molecules are enantiomers, not diastereomers.

Figure: 3.0 (a)

Example 4: Consider the following pairs of molecules and determine whether they are diastereomers or not?

Figure: 4.0

Solution: These molecules are diastereomers. These molecules are not mirror images of one another, and they are non-superimposable, which can be seen by flipping one of the molecules 180 degrees, as shown below in Figure: 4.0 (a). The stereochemistry is the same in one place (the methyls) and is different in another place (the bromines).

Figure: 4.0 (a)

 

Example 5: Consider the following pairs of molecules and determine whether they are diastereomers or not?

Figure: 5.0

 

Solution: These molecules are diastereomers. These molecules are not mirror images of one another, and they are non-superimposable, which can be seen by flipping one of the molecules 180 degrees, as shown below in Figure: 5.0 (a). The stereochemistry is the same in two places (the methyls and the alcohols) and is different in two places (the chlorines and the bromines).

Figure: 5.0 (a)

Example 6: Consider the following pairs of molecules and determine whether they are diastereomers or not?

Figure: 6.0

Solution: These molecules are not diastereomers, because these molecules are mirror images of one another, and they are non-superimposable, which can be seen by flipping one of the molecules 180 degrees, as shown below Figure: 6.0 (a). In one molecule, the bromine is wedged and the methyl is dashed, and in the other molecule, the bromine is dashed and the methyl is wedged. These molecules are enantiomers and not diastereomers.

Figure: 6.0 (a)

Example 7: Consider the following pairs of molecules and determine whether they are diastereomers or not?

Figure: 7.0

Solution: These molecules are not diastereomers, because molecules are mirror images of one another. Additionally, these molecules are non-superimposable because the one on the right, is flipped 180 degrees so that the chlorines are aligned, as shown below in Figure: 7.0 (a), the stereochemistry is different because one chlorine is wedged and the other is dashed. Therefore, these molecules are enantiomers and not diastereomers.

Figure: 7.0 (a)

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