Illustrated Glossary of Organic Chemistry

Ozonolysis: A reaction in which a carbon-carbon pi bond functional group reacts with ozone, resulting in oxidative cleavage. The reactant is usually an alkene or alkyne, but a benzene ring can also be made to react under forcing conditions.

1. O3 2. (CH3)2S

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In alkene ozonolysis with reductive workup, an alkene carbon bearing a hydrogen atom becomes an aldehyde, and an alkene carbon bearing two carbons becomes a ketone.

1. O3 2. HOOH

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In alkene ozonolysis with oxidative workup, an alkene carbon bearing a hydrogen atom becomes a carboxylic acid, and an alkene carbon bearing two carbons becomes a ketone.

1. O3 2. (CH3)2S

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Alkyne ozonolysis converts each alkyne carbon to a carboxylic acid, regardless of reaction workup.