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Chapter 4

Stereoisomerism

Chirality
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror…
Isomerism
Isomers are molecules with the same molecular formula but different structural arrangements. Isomers can be further classified into constitutional…
Stereoisomers
On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are…
Naming Enantiomers
The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a…
Properties of Enantiomers and Optical Activity
It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their…
Molecules with Multiple Chiral Centers
Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one…
Fischer Projections
Learning to draw Fischer projections of molecules and understanding their relevance plays a crucial role in the visual depiction of organic…
Racemic Mixtures and the Resolution of Enantiomers
A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral…
Stereoisomerism of Cyclic Compounds
In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the…
Chirality at Nitrogen, Phosphorus, and Sulfur
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen,…
Prochirality
The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective…
Chirality in Nature
Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a…
Assembly of Gold Nanorods into Chiral Plasmonic Metamolecules Using DNA Origami Templates
The inherent addressability of DNA origami structures makes them ideal templates for the arrangement of metal nanoparticles into complex plasmonic…
Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
This article shows how the COLTRIMS (Cold Target Recoil Ion Momentum Spectroscopy) or the "reaction microscope" technique can be used to distinguish…
Synthesis and Structure Determination of µ-Conotoxin PIIIA Isomers with Different Disulfide Connectivities
Peptides with a high number of cysteines are usually influenced regarding the three-dimensional structure by their disulfide connectivity. It is thus…

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