Ch 6: Alkene + peracid

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Chapter 6: Reactions of Alkenes: Addition Reactions

Epoxidation of Alkenes

Reaction type: Electrophilic Addition

Summary
Overall transformation : C=C to epoxide Reagent : a peracid or peroxyacid, RCO 3H Regioselectivity : not relevant since both new bonds are the same,C-O Stereoselectivity : syn since the two new C-O bonds form at the same time from the peracid. The reaction is an example of a concerted process (all bonding changes occur in one step) Since the reaction is concerted the stereochemistry of the alkene is preserved in the product. For example if the alkyl groups of the alkene are cis- then they are also cis- in the epoxide.

QUESTIONS What other functional group description could be given to an epoxide ? ANSWER What other addition reactions convert an alkene into a three membered ring ? ANSWER MECHANISM FOR REACTION OF ALKENES WITH PERACID A single step reaction involving several changes. Start at the C=C as the nucleophile, make a bond to the slightly electrophilic O, break the weak O-O, make a new C=O ,break the original C=O to make a new O-H bond, break the original O-H to form the new C-O bond ! (phew !) bond to give the epoxide.

Dr. Ian Hunt, Department of Chemistry, University of Calgary

http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch06/ch6-9.html

8/1/2011 10:31:18 PM