Ozonolysis

Ozonolysis uses ozone to cleave carbon–carbon double bonds, forming carbonyl compounds after workup. The products depend on the alkene and the workup conditions.

Criegee mechanism: A mechanism for ozonolysis involving ozonide formation and fragmentation through reactive intermediates. It describes the sequence by which ozone addition leads to carbon–carbon bond cleavage.
Alkene: A hydrocarbon containing at least one carbon–carbon double bond. Alkenes are the characteristic substrates whose double bonds ozonolysis cleaves.
Christian Friedrich Schönbein: A German-Swiss chemist who discovered ozone in 1840. The discovery of ozone made the reagent behind ozonolysis available for later chemical study.
Permanganate oxidation: Oxidation by permanganate that can cleave alkenes or convert them into diols, depending on conditions. It offers an alternative route to alkene cleavage, often under less specialized conditions.
Molozonide: An unstable primary ozonide formed when ozone adds across a carbon–carbon double bond. It is the first cyclic intermediate formed in the commonly described alkene ozonolysis pathway.
Reductive ozonolysis: Alkene ozonolysis followed by reducing workup, typically producing aldehydes and ketones. This form reveals the two carbonyl fragments without usually oxidizing aldehydes further.
Carl Dietrich Harries: A German chemist who developed ozonolysis as a method for studying the structure of unsaturated compounds. His work established the reaction as a tool for identifying double-bond positions.
Dihydroxylation: The addition of two hydroxyl groups across a carbon–carbon double bond to form a vicinal diol. Unlike ozonolysis, dihydroxylation adds oxygen groups without cleaving the carbon–carbon bond.
Carbonyl oxide: A reactive intermediate with a carbon–oxygen double bond and a terminal oxygen atom, also called a Criegee intermediate. Molozonide fragmentation produces this intermediate before ozonide formation.
Oxidative ozonolysis: Alkene ozonolysis followed by oxidizing workup, which converts aldehyde products into carboxylic acids. This variant gives different products from the same alkene by changing the workup.

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