| Qu 1: |
Epoxides can be formed in two ways, either epoxidation
of an alkene or via the halohydrin. |
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(a) What is the stereochemistry of epoxidation ? |
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(b) If Z-2-butene is treated with peracetic acid, what is the stereochemistry
of the epoxide ?
Assign the configurations to any chiral centers. |
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(c) If E-2-butene is treated with peracetic acid, what is the stereochemistry
of the epoxide ?
Assign the configurations to any chiral centers. |
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(d) What is the stereochemistry of halohydration ? |
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(e) If Z-2-butene is treated with HOCl then NaOH, what is the stereochemistry
of the epoxide ? |
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| Qu 2: |
What is the major product from the reaction of ethylene oxide with
each of the following ? |
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| (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 |
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| Qu 3: |
What is the major product from the reaction of propylene oxide with
each of the reagents in Qu 2 ? |
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| Qu 4: |
Draw a curly arrow mechanism to rationalize the stereochemistry of
the following reactions: |
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