Categories: Chemistry

Difference Between Enantiomers and Diastereomers

The Basic Difference Between Enantiomers And Diastereomers is that Enantiomers have identical physical properties like melting and boiling points, refractive indexes, densities, etc they have also identical chemical properties. while Diastereomers have different physical properties like melting and boiling points, densities, etc.

In this post, you are going to learn about the Enantiomers vs. Diastereomers step by step with Diagram.

This post includes:

  • An overview
  • Difference table
  • What are Enantiomers
  • What are Diastereomers
  • Lots more

So if you want to get benefits from this post you’ll love this post.

Let’s Dive right in..

An Overview

While studying organic chemistry many of the student’s invasions a problem in Enantiomers vs Diastereomers. without understanding the differences you need to master a clear understanding of stereochemistry and the correct product for future reactions determination will not be possible. 

the Isomers are majorly grouped into two sections such as stereoisomers and structural isomers. Stereoisomers differ in the spatial arrangement in structures while Structural isomers have the same molecular formula,  but different order and bond connections.

from stereoisomers and structural isomers, stereoisomers are further subdivided into two groups known as Enantiomers and Diastereomers. the Enantiomers are found as mirror images of one another having chiral molecules and Diastereomers are stereomer molecular compounds and are neither mirrored images of each other nor superimposable.  

as mirror images of each other, they cannot be stacked on top of each other and also cannot be lined up exactly as same. this article will lead you to the exact way how to differentiate between Enantiomers And Diastereomers.

Difference Between Enantiomers And Diastereomers in Tabular Form

Enantiomers

Diastereomers

Enantiomers are types of stereoisomers that are mirror images of each other

Diastereomers are types of stereoisomers that do not mirror images of each other

they are non-superimposable mirror images of each other.

they are also non-superimposable but are not mirror images of each other.

Enantiomers Have identical physical properties except for the ability to rotate plane-polarized light and interaction with eight and interaction with other chiral compounds.

Diastereomers have different physical and chemical properties

Enantiomers are always Present in pairs

Diastereomers can be present in several molecules

they have one or more stereocenters.

they have two or more than two stereocenters.

have a Similar molecular shape

has a different molecular shape

they all pass optical activity and have equal but opposite angles of rotation.

they do not all pass the optical activity and also do not have an equal angle of rotation.

The shapes of molecules are approximately similar.

present in different molecular shapes.

can not be separated by crystallization, chromatography, etc.

can be separated by fractional distillation, chromatography, etc.

always have a different R, S-configuration.

always have the same R, S-configuration at least at one stereocenter.

Lactic acid is a common example. 

Tartaric acid is a common example.

What is Chirality

the condition of chiral is known as Chirality. and applies to the elements which cannot be superimposed with their own mirror image.in chemistry, chirality is associated with asymmetry. an element or object can be chiral when it is distinguished from the reflected image of his own. 

while an achiral is a phenomenon reversible of chiral in which overlapping with the mirror image can be possible.  those molecules who are stereoisomers, they are essentially chiral structure. when four different molecule groups are connected with one central carbon these molecules are in chirality form if they fulfill the condition of should be chemically distinguishable.  this carbon is known as chiral carbon.

What are Enantiomers

The enantiomers are stereoisomers whose molecules are non-overlapping mirror images of each other. Enantiomers are only possible with molecules that are chiral. A chiral molecule is one that is not identical to its mirror image. 

For a molecule to be chiral, it must have a tetrahedral carbon atom with four different groups attached to it. This carbon atom is known as the stereocenter. Chiral molecules create mirror images that are not superimposable. Therefore, the molecule and the mirror image are enantiomers of each other. The following is an example of a compound that forms enantiomers.

We usually name enantiomers using the R and S systems. Enantiomers do not have different boiling points, melting points, solubilities, different infrared spectra, etc. All these chemical and physical properties of the enantiomers are similar because the intermolecular forces are similar in both isomers. 

They are separated only by their different behaviors towards in-plane polarized light. That is, the enantiomers rotate the plane of polarized light in opposite directions. 

However, they rotate the light in equal amounts. Due to their effect on polarized light, enantiomers are optically active. The equimolar mixture of two enantiomers is a racemic mixture. A racemic mixture does not show any rotation of polarized light; therefore, it is optically inactive.

What are Diastereomers

Diastereomers are stereoisomers whose molecules are not mirrored images of each other. For example, the cis and trans isomers are diastereomers. Here, the connectivity of the atoms is the same.

In the example above, both compounds have a carbon-carbon double bond. For each carbon, a methyl group and a hydrogen atom are connected. Cis and trans molecules differ only in the way the atoms are arranged in space. That is, in the cis isomer, both hydrogens are on the same side of the carbon double bond. 

However, in the trans isomer, the hydrogen atoms are on either side of the carbon double bond. Also, the two structures are not mirrored images of each other. Therefore, they are diastereomers. However, cis and trans molecules are not the only type of diastereomers that we can find.

Difference Between Enantiomers and Diastereomers

Enantiomers are stereoisomers that are non-superimposable mirror images.

Diastereomers are stereoisomers that are non-superimposable and are not mirror images. 

Number of Isomers

Enantiomers are always present in pairs.

Diastereomers can be present as several molecules that are diastereomers of each other.

Morphology

The shape of the molecule is similar to enantiomers.

Diastereomers have different molecular shapes.

Physical Properties

Enantiomers have identical physical properties except the ability to rotate plane-polarized light.

Diastereomers have distinct physical properties.

Conclusion

isomers are divided into structural isomers and stereoisomers. stereoisomers are optical active due to chiral centers. the stereoisomers are further grouped into Enantiomers and Diastereomers. the configuration of Enantiomers is differed at every stereocenter and is mirror images of each other. Diastereomer molecules are not mirrored images of each other because of the spatial arrangements of their atoms. the major Difference Between Enantiomers And Diastereomers is that Enantiomers are mirror images and Diastereomers are not mirror images. 

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