Return to Contents Chapter 16: Ethers, Epoxides and Sulfides Ch 16 contents
Epoxide Questions
 
Qu 1: Epoxides can be formed in two ways, either epoxidation of an alkene or via the halohydrin.
(a) What is the stereochemistry of epoxidation ?
(b) If Z-2-butene is treated with peracetic acid, what is the stereochemistry of the epoxide ? 
     Assign the configurations to any chiral centers.
(c) If E-2-butene is treated with peracetic acid, what is the stereochemistry of the epoxide ?
     Assign the configurations to any chiral centers.
(d) What is the stereochemistry of halohydration ?
(e) If Z-2-butene is treated with HOCl then NaOH, what is the stereochemistry of the epoxide ?
Qu 2: What is the major product from the reaction of ethylene oxide with each of the following ?
(a) H3O+ (b) aq. NaOH
(c) NaOCH3 in CH3OH (d) CH3OH with cat. H2SO4
(e) LiAlH4 / THF then acidic work-up (f)  PhMgBr then acidic work-up
(g)  NaSCH3 in ether, then acidic work-up
Qu 3: What is the major product from the reaction of propylene oxide with each of the reagents in Qu 2 ?
Qu 4: Draw a curly arrow mechanism to rationalise the stereochemistry of the following reactions:
 

Answers ?


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organic chemistry © Dr. Ian Hunt, Department of Chemistry University of Calgary