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Related Concept Videos

Oxidative Cleavage of Alkenes: Ozonolysis01:46

Oxidative Cleavage of Alkenes: Ozonolysis

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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.
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Alkynes to Carboxylic Acids: Oxidative Cleavage02:01

Alkynes to Carboxylic Acids: Oxidative Cleavage

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Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
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Hess's Law03:40

Hess's Law

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There are two ways to determine the amount of heat involved in a chemical change: measure it experimentally, or calculate it from other experimentally determined enthalpy changes. Some reactions are difficult, if not impossible, to investigate and make accurate measurements for experimentally. And even when a reaction is not hard to perform or measure, it is convenient to be able to determine the heat involved in a reaction without having to perform an experiment.
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Radical Formation: Homolysis00:54

Radical Formation: Homolysis

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A bond is formed between two atoms by sharing two electrons. When this bond is broken by supplying sufficient energy, either two electrons can be taken up by one atom forming ions by the cleavage called heterolysis, or the two electrons are shared by two atoms, with one each creating radicals by the cleavage called homolysis.
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Preparation of Epoxides03:00

Preparation of Epoxides

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Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy...
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Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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Related Experiment Video

Updated: May 3, 2026

In situ FTIR Spectroscopy as a Tool for Investigation of Gas/Solid Interaction: Water-Enhanced CO2 Adsorption in UiO-66 Metal-Organic Framework
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In situ FTIR Spectroscopy as a Tool for Investigation of Gas/Solid Interaction: Water-Enhanced CO2 Adsorption in UiO-66 Metal-Organic Framework

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Ozone dissociation to oxygen affected by Criegee intermediate.

Wen-Mei Wei1, Ren-Hui Zheng, Yue-Li Pan

  • 1Department of Chemistry, College of Basic Medicine, Anhui Medical University , Hefei, Anhui 230032, P. R. China.

The Journal of Physical Chemistry. A
|February 18, 2014
PubMed
Summary

New reaction pathways for Criegee intermediates (CI) and formaldehyde with ozone were discovered. These findings suggest CI may not efficiently catalyze ozone dissociation into oxygen.

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Time-resolved Photophysical Characterization of Triplet-harvesting Organic Compounds at an Oxygen-free Environment Using an iCCD Camera
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Area of Science:

  • Atmospheric Chemistry
  • Quantum Chemistry
  • Chemical Kinetics

Background:

  • Criegee intermediates (CI) play a crucial role in atmospheric chemistry.
  • Understanding CI reactions with ozone is vital for air quality modeling.
  • Previous mechanisms for CI and formaldehyde reactions with ozone exist.

Purpose of the Study:

  • To investigate potential energy surfaces for H2COO + O3 and H2CO + O3 reactions.
  • To identify new reaction pathways and compare them with existing mechanisms.
  • To assess the role of CI in ozone dissociation.

Main Methods:

  • High-level ab initio calculations using CCSD(T)/aug-cc-pVDZ//B3LYP/6-311++G(2d,2p).
  • Detailed potential energy surface mapping.
  • Transition state theory analysis.

Main Results:

  • Novel reaction mechanisms for H2COO + O3 and H2CO + O3 were identified.
  • A lower energy pathway for H2COO + O3 dissociation to formaldehyde and oxygen was found.
  • High energy barriers were calculated for H2CO + O3 to produce H2COO and O2.

Conclusions:

  • The newly found mechanism facilitates the dissociation of H2COO + O3.
  • CI is unlikely to catalyze ozone dissociation to oxygen due to high energy barriers in the H2CO + O3 pathway.
  • These findings offer new insights into atmospheric reaction kinetics and ozone chemistry.