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Enantiomers - Overview, Structure & Function, Properties, FAQs

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Enantiomers - Overview, Structure & Function, Properties, FAQs

Edited By Team Careers360 | Updated on Jun 17, 2022 04:06 PM IST

Enantiomers: What are they?

Enantiomers is one of the most important concepts to consider when considering stereochemistry.
Molecular stereochemistry:
Three-dimensionality is the meaning of the word stereo. The study of stereochemistry focuses on how the orientation of its atoms in space affects a molecule. Stereoisomerism is a key concept in stereochemistry, which relates to chemical compounds with the same molecular formula but different spatial configurations. Diastereomers and enantiomers are broad categories of stereoisomers.

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An optically active system:

Molecules that are capable of rotating plane-polarized light are known as optically active molecules.

The racial structure

Racemic mixtures are equimolar mixtures of dextrorotatory and laevorotatory compounds, i.e., 50% Dextrose and 50% Leo.

Centre Chiral:

The carbon atom attached directly to four distinct groups is called a chiral carbon or chiral centre.

Comparison of enantiomers and chiral compounds

It can be described as the detection of the difference between the two enantiomers of chiral molecules. Enantiomers have the same physical properties that can be used to separate molecular species, so they are hard to distinguish.

The only way to observe physical differences is through interactions with secondary species capable of discriminating.

Enantiomerically oriented molecules are known as chiral molecules.

An enantiomer is a pair of molecules that is a mirror image of one another but cannot overlap or superimpose one onto the other.

Every other aspect of their chemical composition is the same. Enantiomers, or dual isomers, are distinguished by the direction in which they rotate polarized light when they are dissolved in solution; these rotations are labelled as Dextrose (d or +) or Leo (l or -).

Two enantiomers present in equal proportions form a racemic mixture because their optical activities cancel one another. They do not rotate polarized light because both enantiomers are involved simultaneously.

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Enantiomers: Structure and Function

In general, chirality occurs when an atom is tetrahedrally coordinated and bound to four different substituents, as shown in the figure below.

An enantiomer is a mirror image of another that cannot be superimposed.

In the biological world, chirality is the property that allows a molecule to exist as a pair of enantiomers, thus allowing it not to superimpose on its mirror image. The opposite is true for molecules that are achiral when viewed from their mirror image.

There is an enantiomer in every single molecule containing an atom that is tetrahedrally bound to four different substituents.

There is a crucial difference between all four substituents. If any two of them were identical, the structure would become superimposed onto its mirror image, giving rise to the achiral structure. Heterogeneous centres or simply stereo centres are atoms connected to four different atoms.

The stereo enters, which is a widely used although the somewhat misleading alternative term, is a localized property of the molecule that cannot be localized around a single atom or an atomic grouping.

Stereo enters are not required for molecules to show chirality; they're just the most common reason.

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Enantiomer properties

The physical properties of enantiomers, such as melting point, boiling point, infrared emission, and NMR spectra, are usually identical. But it is important to realize that even though the melting point, etc., of one enantiomer, is the same as that of the other enantiomer, it is the melting point of the mixture that will differ.

Since the intermolecular interactions between molecules of opposite stereochemistry that are between R and S molecules may be different from those between molecules of like stereochemistry between molecules of either R or S stereochemistry. Optical rotation, the most common chiroptical technique, is the only technique capable of distinguishing the two enantiomers of a compound. One difference between enantiomers is the sign of the torsional angles, which is primarily responsible for a molecule's chiroptical properties.

Purity of optical light:

As an example, let us consider a non-racemic mixture of enantiomers with an optical impurity, and measure how the optical rotation changes for a mixture of compounds with known rotation. This would allow us to determine its optical purity and determine the ratio of the enantiomers. You can calculate the kind of pure enantiomer by dividing the observed specific rotation of a mixture with a pure enantiomers' rotation. If * is the specific rotation, then-Optical Purity = Spectral rotation of the mixture / observed Rotation of pure enantiomers

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NCERT Chemistry Notes:

Frequently Asked Question (FAQs)

1. Q1. Differentiate between enantiomers and diastereomers.

 Enantiomers and diastereomers differ in the following ways:

Enantiomers

Diastereomers

The mirror images of these structures cannot be superimposed.

It is impossible to superimpose or mirror a pair of molecules.

Both physical and chemical properties are the same.

A melting point, boiling point, dipole moment, etc. make it possible to separate fractions based on physical characteristics.

The optical properties make them active.

Optical activity may or may not be present.

Formation of racial mixtures.

Racemic mixtures do not form.

2. Q2. Racemic mixtures can be optically active? Explain.

Equal proportions of the d and l enantiomers are present in racemic mixtures, i.e., 50:50. The conversion angle of plane-polarized light is an indicator of the optical activity of a substance. Compounds can either be dextrorotatory or laevorotatory, depending on their rotation direction. Due to the fact that racemic mixtures consist of oppositely oriented enantiomers, the net rotation is zero. There is therefore no way to rotate plane-polarized light, and there is no optical activity. An optically active racemic mixture can therefore not exist.

3. Q3. Explain Four Different Types of Stereoisomers.

There are four types of stereoisomers:

  1. A conformational isomer is an isomer that can be converted to another by rotating the structure about one or more single bonds.

  2. The Cis-Trans isomers refer to molecules with the same formula but with different inorganic functional groups. There are two types of groups at an atom: those on the same side and those on the other side. Therefore, geometrical isomerism and configurational isomerism are synonymous with trans-cis isomerism.

  3. The term diastereomer refers to a pair of molecules that are not superimposed upon one another.

  4. An enantiomer is the mirror image of its mirror image; optical isomers that have distinct structures.

4. Q4. Enantiomers are different in what way?

A key stereo genic feature is a difference in structure between the two enantiomers (R or S). Achiral environments exhibit identical physical and chemical properties between the enantiomers. In addition, different chiral molecules interact differently with enantiomers because the plane of polarized light rotates into opposite angles.

5. Q5. Diastereomers: What do they mean?

Diastereomers are stereoisomers that do not repeat each other's images, nor can they be superimposed. A diastereomer may be a stereoisomer of two or more stereo enters. The determination of diastereomers between molecules can sometimes be difficult.

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