Ozonolysis:alkeneoralkyneiscleavedbyreactingitwithozoneExample:

*Mechanism:

O3---------->synadditionofO3NeitherMarkovnikovnoranti-Markovnikov(O3issymmetrical)NeitheralkenenorO3iselectrophile(bothgiveandreceiveelectrons)

------------>Oxygenlonepairsrepelcausingmoleculetobreakapartandrearrange

(CH3)2S-------->

Finalstereochemistry:Neithersynnoranti

Overallmechanism:SynadditionofO3--->Rearrange--->Add(CH3)2S--->Finalproductcleavedbyozone*Usefultip:theproductscanbefound(withoutgoingthroughthemechanism)byslicingthealkeneandaddingoxygentotheendsoftheopenalkene

WorksCited

Hardinger,Steven.“Chemistry14DLectureSupplement”4thEd.HaydenMcNeil.2016.Print.