s20 2011 week 3 day 4-post

s20 2011 week 3 day 4-post - Chemistry S-20ab Week 3...

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Opening Epoxides with Grignard Reagents Provide a mechanism that shows how the following epoxide reacts with the indicated Grignard reagent: mCPBA O CH 3 MgBr H + workup OH CH 3 This reaction is quite useful for synthesis, because it forms a new carbon-carbon bond . Provide a synthetic route for the following transformation: OH OH Reading : Section 11.5 Chemistry S-20ab Week 3 1 ±²
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!"#$%&'() +,-./0 1##2 3 455 Synthesis of Glycols (Vicinal Diols) from Epoxides Glycols can be synthesized from epoxides. What is the overall stereochemistry of the following transformation? In general, acid-catalyzed hydrolysis of epoxides is preferable to base-catalyzed hydrolysis, because base-catalyzed hydrolysis can result in polymerization : 6"%& 789)$#(%:/'%8; (#/<'%8; %& #='(#$#9) #=8'"#($%<> /;? </; 0# ?/;@#(8A&B "#$%&'( C +#<'%8; 44DE OH OH mCPBA H 2 O, H + OH + O HO O O O etc.
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Synthesis of Glycols (Vicinal Diols) from Alkenes There is a direct route to synthesis of glycols from alkenes using osmium tetroxide, OsO 4 . Draw the curved arrows for the following reaction. What is the overall stereochemistry of this reaction? Os O O O O = OsO 4 OsO 4 O Os O O O (+/–) (not isolated) H 2 O OH OH (+/–) Reading : Section 11.5 Chemistry S-20ab Week 3 1 ±²
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Cleavage of Glycols: It ! s Kinda Like Ozonolysis
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This note was uploaded on 07/28/2011 for the course CHEM S20 taught by Professor Evan during the Spring '11 term at Belhaven.

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s20 2011 week 3 day 4-post - Chemistry S-20ab Week 3...

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