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Oxidative Cleavage of Alkenes: Ozonolysis

Oxidative Cleavage of Alkenes: Ozonolysis

In ozonolysis, ozone is used to cleave a carbon–carbon double bond to form aldehydes and ketones, or carboxylic acids, depending on the work-up.
Ozone is a symmetrical bent molecule stabilized by a resonance structure.

Exceptions to the Octet Rule

Exceptions to the Octet Rule

Many covalent molecules have central atoms that do not have eight electrons in their Lewis structures. These molecules fall into three categories:

Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems

Phase I Reactions: Oxidation of Carbon-Heteroatom and Miscellaneous Systems

Oxidative reactions are pivotal in metabolizing numerous compounds, including pharmaceutical drugs. These reactions often occur in carbon-heteroatom systems, such as carbon-nitrogen, carbon-sulfur, and carbon-oxygen.
In carbon-nitrogen systems, aliphatic and aromatic amines can undergo oxidative reactions. Secondary and tertiary amines, like those found in tricyclic antidepressants, can undergo N-dealkylation, a process that involves the oxidation of the alkyl group. In addition, oxidative...

Frost Circles for Different Conjugated Systems

Frost Circles for Different Conjugated Systems

The inscribed polygon method is consistent with Hückel’s 4n + 2 rule and helps to learn whether the given cyclic compound is aromatic or not. The compound is stable and aromatic if every bonding molecular orbital (MO) is completely filled with a pair of electrons. However, if the non-bonding or antibonding orbitals are filled with electrons, the compound is unstable and not aromatic. Consider the Frost circle diagrams for cycloalkenes containing 4 to 8 carbons.

Mass Spectrometry: Cycloalkane Fragmentation

Mass Spectrometry: Cycloalkane Fragmentation

In mass spectrometry, cycloalkanes exhibit distinct fragmentation patterns due to the inherent stability of their molecular ions compared to linear or branched alkanes. The ring structure of cycloalkanes provides additional stability to the molecular ions, often resulting in prominent ion peaks in the mass spectrum.
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Mass Spectrometry: Molecular Fragmentation Overview

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Related Experiment Video

Updated: Jul 12, 2026

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Published on: April 8, 2020

Large odd-numbered carbon clusters from fullerene-ozone reactions.

S W McElvany, J H Callahan, M M Ross

Science (New York, N.Y.)

|June 11, 1993

Summary

Odd-numbered carbon clusters like C119, C129, and C139 were discovered. These fullerene derivatives suggest a new method for fullerene functionalization via ozone reactions.

Area of Science:

Chemistry
Materials Science

Background:

Fullerenes, such as C60 and C70, are allotropes of carbon with unique cage-like structures.
Fullerene soot and toluene extracts are common sources for fullerene research.
Ozone reactions are known to modify carbon structures.

Purpose of the Study:

To investigate the formation and properties of odd-numbered carbon clusters.
To explore the role of ozone in fullerene reactions.
To identify potential new pathways for fullerene functionalization.

Main Methods:

Mass spectrometry analysis of fullerene soot extracts.
Ozone-fullerene reaction product analysis.
Characterization of gas-phase ions.

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Published on: September 18, 2016

Spatial Separation of Molecular Conformers and Clusters

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

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Last Updated: Jul 12, 2026

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Computation of Atmospheric Concentrations of Molecular Clusters from ab initio Thermochemistry

Published on: April 8, 2020

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

Published on: September 18, 2016

Spatial Separation of Molecular Conformers and Clusters

Spatial Separation of Molecular Conformers and Clusters

Published on: January 9, 2014

Main Results:

Observation of odd-numbered carbon clusters: C119, C129, and C139.
Specific formation pathways identified: C119 from ozone-C60, C139 from ozone-C70, and all three from ozone-(C60/C70) reactions.
These clusters behave as stable gas-phase ions, analogous to fullerenes, and represent dimers minus one carbon atom.

Conclusions:

The study reveals a novel route for fullerene derivatization.
Ozone-catalyzed cage-opening reactions offer a new method for synthesizing functionalized fullerenes.
The discovery of these odd-numbered clusters expands the known fullerene family and their reactivity.