ozonolysis - ucla chemistry and biochemistryharding/summaries/14d24.pdf · ozonolysis: alkene or...
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![Page 1: Ozonolysis - UCLA Chemistry and Biochemistryharding/summaries/14D24.pdf · Ozonolysis: alkene or alkyne is cleaved by reacting it with ozone Example: *Mechanism: O 3 -----> syn addition](https://reader034.vdocuments.site/reader034/viewer/2022050902/5a7868c97f8b9a77438c816b/html5/thumbnails/1.jpg)
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
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WorksCited
Hardinger,Steven.“Chemistry14DLectureSupplement”4thEd.HaydenMcNeil.2016.Print.