ozonolysis - ucla chemistry and biochemistryharding/summaries/14d24.pdf · ozonolysis: alkene or...

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Ozonolysis: alkene or alkyne is cleaved by reacting it with ozone Example: *Mechanism: O3 ----------> syn addition of O3 Neither Markovnikov nor anti- Markovnikov (O3 is symmetrical) Neither alkene nor O3 is electrophile (both give and receive electrons) ------------> Oxygen lone pairs repel causing molecule to break apart and rearrange (CH3)2S --------> Final stereochemistry: Neither syn nor anti Overall mechanism: Syn addition of O3 ---> Rearrange ---> Add (CH3)2S ---> Final product cleaved by ozone *Useful tip: the products can be found (without going through the mechanism) by slicing the alkene and adding oxygen to the ends of the open alkene

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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

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

Page 2: 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

WorksCited

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

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