Editing Ozone (section)

===With alkenes and alkynes===
{{Main|Ozonolysis}}
Alkenes can be oxidatively cleaved by ozone, in a process called [[ozonolysis]], giving alcohols, aldehydes, ketones, and carboxylic acids, depending on the second step of the workup.

[[File:General reaction equation of ozonolysis.svg|class=skin-invert-image|frameless|upright=2.2|center|General reaction equation of ozonolysis]]

Ozone can also cleave alkynes to form an [[acid anhydride]] or [[diketone]] product.<ref>{{cite book |last=Bailey |first=P. S. |chapter=Chapter 2 |title=Ozonation in Organic Chemistry |volume=2 |publisher=Academic Press |location=New York, NY |year=1982 |isbn=978-0-12-073102-2}}</ref> If the reaction is performed in the presence of water, the anhydride hydrolyzes to give two [[carboxylic acid]]s.

:[[File:Ozonolysis-alkyne.png|class=skin-invert-image|none|450px]]

Usually ozonolysis is carried out in a solution of [[dichloromethane]], at a temperature of −78&nbsp;°C. After a sequence of cleavage and rearrangement, an organic ozonide is formed. With reductive workup (e.g. [[zinc]] in [[acetic acid]] or [[dimethyl sulfide]]), ketones and aldehydes will be formed, with oxidative workup (e.g. aqueous or alcoholic [[hydrogen peroxide]]), carboxylic acids will be formed.<ref name="OrgChem">{{cite book
|title=Organic Chemistry, 9th Edition
|chapter=Chapter 8 Alkenes and Alkynes – Part II: Addition Reactions and Synthesis
|author1=Solomons, T.W. Graham |author2=Fryhle, Craig B.
|name-list-style=amp |publisher=Wiley
|year=2008
|isbn=978-0-470-16982-7
|page=344
}}</ref>