ozonolysis - ucla chemistry and biochemistryharding/summaries/14d24.pdf · ozonolysis: alkene or...
Post on 05-Feb-2018
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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.
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