Ozonolysis is one of the simplest of all organic reactions to perform, yet the ozonolysis mechanism often leads to confusion when presented in undergraduate Organic Chemistry. If the reaction is so simple, then why is the ozonolysis mechanism so challenging? Well, there’s the 1,3-dipolar cycloaddition followed by a retro 1,3-cycloaddition and recombination via a second 1,3-cycloaddition leading to an intermediate with an electrophilic oxygen that gets attacked by a sulfur nucleophile. Sounds kinda like listening to someone’s story of getting from point A to point Z via a tour through La La Land, huh?
