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Related Concept Videos

Racemic Mixtures and the Resolution of Enantiomers02:30

Racemic Mixtures and the Resolution of Enantiomers

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A racemic mixture, or racemate, is an equimolar mixture of enantiomers of a molecule that can be separated using their unique interaction with chiral molecules or media. Racemic mixtures are denoted by the (±)- prefix. This ‘optical rotation descriptor’ applies to the whole solution of a racemic mixture rather than a specific stereoisomer. Enantiomers typically have the same physical and chemical properties. Hence, they are not easily separable. However, enantiomers can exhibit...
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Stereochemical Effects of Enolization01:12

Stereochemical Effects of Enolization

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The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
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SN1 Reaction: Stereochemistry02:15

SN1 Reaction: Stereochemistry

10.1K
This lesson provides an in-depth discussion of the stereochemical outcomes in an SN1 reaction.
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
10.1K
Radical Formation: Addition00:47

Radical Formation: Addition

2.1K
Radicals can be formed by adding a radical to a spin-paired molecule. This is typically observed with unsaturated species, where the addition of a radical across the π bond leads to the production of a new radical by dissolving the π bond. For example, the addition of a Br radical to an alkene yields a carbon-centered radical.
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...
2.1K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

16.0K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
16.0K
Naming Enantiomers02:21

Naming Enantiomers

25.2K
The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three...
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Related Experiment Video

Updated: Jan 4, 2026

Label-Free Imaging of Lipid Storage Dynamics in Caenorhabditis elegans using Stimulated Raman Scattering Microscopy
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Racemisation in Chemistry and Biology.

Andrew Ballard1, Stefania Narduolo1, Hiwa O Ahmed1,2

  • 1School of Chemistry, Cardiff University, Main Building, Park Place, Cardiff, CF10 3AT, UK.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|November 12, 2019
PubMed
Summary

Racemisation, the conversion of a compound into a mixture of enantiomers, is critical for drug development. This review examines racemisation in biological and chemical aqueous systems, offering insights into predicting and controlling this process.

Keywords:
aqueous stabilitydrug discoverykineticsreaction mechanismsstereochemistry

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Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
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Methods to Identify the NMR Resonances of the 13C-Dimethyl N-terminal Amine on Reductively Methylated Proteins
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Area of Science:

  • Stereochemistry
  • Biochemistry
  • Medicinal Chemistry

Background:

  • Enantiomers possess distinct biological activities, making their stability crucial.
  • Racemisation in aqueous solutions is a key factor in drug efficacy and safety.
  • Understanding racemisation mechanisms is vital for pharmaceutical development.

Purpose of the Study:

  • To review and critically analyze data on racemisation processes in biological and chemical aqueous environments.
  • To discuss experimental and computational methods for determining racemisation rates.
  • To explore strategies for controlling or promoting racemisation.

Main Methods:

  • Comprehensive literature review of existing studies on racemisation.
  • Critical analysis of mechanistic and kinetic data.
  • Discussion of experimental techniques for rate constant determination.
  • Examination of computational studies for risk prediction.

Main Results:

  • Racemisation occurs under various conditions: enzymatic, in serum albumin, and chemically (acid/base).
  • Enzymatic racemisation mechanisms differ from those in bulk water.
  • Experimental and computational methods provide quantitative predictions of racemisation risk.

Conclusions:

  • Racemisation liability is a critical parameter for compounds with differing enantiomer properties.
  • Understanding diverse racemisation pathways (enzymatic vs. chemical) is essential.
  • Predictive models and controlled racemisation strategies are key for pharmaceutical applications.