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Related Concept Videos

Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
Stereoisomerism02:52

Stereoisomerism

Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
Catalysis02:50

Catalysis

The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.

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Related Experiment Video

Updated: Jun 20, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Atmospheric heterogeneous stereochemistry.

Grace Y Stokes1, Ehow H Chen, Avram M Buchbinder

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.

Journal of the American Chemical Society
|September 24, 2009
PubMed
Summary
This summary is machine-generated.

Stereochemistry significantly impacts atmospheric reactions. Chiral organic compounds on aerosols react differently with ozone based on their orientation, affecting product formation and potentially enabling source attribution.

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Production and Measurement of Organic Particulate Matter in the Harvard Environmental Chamber
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Production and Measurement of Organic Particulate Matter in the Harvard Environmental Chamber

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Single-throughput Complementary High-resolution Analytical Techniques for Characterizing Complex Natural Organic Matter Mixtures

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Related Experiment Videos

Last Updated: Jun 20, 2026

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers
08:51

Coulomb Explosion Imaging as a Tool to Distinguish Between Stereoisomers

Published on: August 18, 2017

Production and Measurement of Organic Particulate Matter in the Harvard Environmental Chamber
09:46

Production and Measurement of Organic Particulate Matter in the Harvard Environmental Chamber

Published on: November 18, 2018

Single-throughput Complementary High-resolution Analytical Techniques for Characterizing Complex Natural Organic Matter Mixtures
09:38

Single-throughput Complementary High-resolution Analytical Techniques for Characterizing Complex Natural Organic Matter Mixtures

Published on: January 7, 2019

Area of Science:

  • Atmospheric Chemistry
  • Organic Geochemistry
  • Chemical Kinetics

Background:

  • Many atmospheric organic compounds are chiral and surface-active.
  • The influence of stereochemistry on atmospheric heterogeneous oxidation remains largely unexplored.
  • Understanding these reactions is crucial for atmospheric modeling and source apportionment.

Purpose of the Study:

  • To investigate the role of stereochemistry in the heterogeneous oxidation of chiral organic molecules by ozone.
  • To quantify the impact of molecular orientation on reaction rates and product formation.
  • To assess the potential for stereochemical enrichment in atmospheric oxidation products.

Main Methods:

  • Utilized nonlinear vibrational surface spectroscopy to study quinuclidine diastereomers on silica substrates.
  • Simulated tropospheric conditions with varying ozone concentrations (10^11 to 10^13 molecules/cm^3) at 1 atm helium.
  • Performed kinetic studies to determine heterogeneous ozonolysis rate constants.

Main Results:

  • Diastereomers with reactive C=C bonds oriented towards the gas phase reacted 2 times faster with ozone.
  • Observed differences in reaction rates suggest stereochemistry influences heterogeneous ozonolysis.
  • Potential for stereochemical enrichment of oxidation products (gaseous or surface-bound) was identified.

Conclusions:

  • Molecular stereochemistry and orientation are critical factors in the heterogeneous reactions of chiral organic aerosols with ozone.
  • Kinetic resolution during ozonolysis can lead to stereochemically enriched products.
  • These findings have implications for understanding atmospheric processes, prebiotic chemistry, and identifying sources of emissions.