Chem 317 - Set 3 extra problem solutions

Chem 317 - Set 3 extra problem solutions - Cl O CHEM 317 PS...

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CHEM 317 PS 3 Ethers and Epoxides-Solutions 1. a) ethyl isopropyl ether or 2-ethoxypropane b) sec -butyl t -butyl ether or 2- t -butoxybutane 2a) OH TsCl py OTs O - NaH OH O b) 1) BH 3 -THF 2) H 2 O 2 /NaOH OH 1) Na 2) CH 3 I O c) 1) Hg(OAc) 2 , CH 3 OH 2) NaBH 4 O d) OH heat H 2 SO 4 HBr Br Mg, ether MgBr mCPBA O 1) 2) H + , H 2 O OH + enant.
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CHEM 317 PS 3 Ethers and Epoxides-Solutions 3a) OH + Br b) I OH c) O d) HO Ph H 2 SO 4 heat Ph mCPBA CH 2 Cl 2 O Ph Cl HO NaOH NaOH C 5 H 10 O C 5 H 10 O e) 1) BH 3 -THF 2) H 2 O 2 / - OH 1) Hg(OAc) 2 /H 2 O 2) NaBH 4 Cl O OH
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Unformatted text preview: Cl O CHEM 317 PS 3 Ethers and Epoxides-Solutions 4. O H + O H + H 2 O O OH HO OH S H 2 O H H acid-catalyzed O base OH O OH H O H HO OH + -OH (+H + ) Acid catalyzed involves attack at the chiral carbon and gives inversion of configuration. For the base catalyzed opening, no bond to the chiral center is broken and the configuration is retained. R R R...
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Chem 317 - Set 3 extra problem solutions - Cl O CHEM 317 PS...

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