03 - O O OH OMe O OMe O OH Br O Ph HO OH HO O S O OH O H H...

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O O O MgBr Br O OH Br Br OH OH OH OH OH OH Chem 212 Alcohol Problems 3 1 . Provide the product, starting materials, or reagents, as appropriate. a) Br 1. MeMgBr 2. H 3 O + b) O 1. LiAlH 4 2. H 3 O + c) 1. 2. H 3 O + 1. Mg, ether 2. 3. H 3 O + O d) e) OH OMe NaH f) g) h) SOCl 2 PCC O PBr 3 HI i) j) O k) HO Ph l) Na 2 Cr 2 O 7 m) O o) 1. MeMgBr 2. H 3 O + p) HO Ph HI q) NaOMe HO Ph O r) MeCO 3 H s) t) u) PCC v) 1. NaH 2. MeBr w) H 2 SO 4 MeOH 2 . Provide detailed mechanisms for the following reactions OH OH racemic OH racemic * OH PBr 3 O OTMS Cl O Br I OH O H OH Me OH OH I racemic racemic racemic O racemic HO Et MeO Ph OMe OH 1. PhMgBr 2. H 3 O+ NR MgBr O
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Unformatted text preview: O O OH OMe O OMe O OH Br O Ph HO OH HO O S O OH O H H OH 2 O S O OH O H b) d) c) a) OMe OH e) f) OH Ph OH O Me H H 3 O H 2 O OMe OH HOMe "S N 1" H Br H 3 O only trans isomer OH 2 mix of cis and trans "S N 2" Br Ph O H 3 O H 2 O H 2 O OH OH OH OH 1. H 2 SO 4 , H 2 O 2.TMSCl, TEA 1.TMSCl, TEA 2. Mg, ether 3. EtCHO 4. H 3 O + 1.TMSCl, TEA 2. EtMgBr 3. H 3 O +...
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This note was uploaded on 06/04/2009 for the course CHEMISTRY CHEM 2020 taught by Professor Mr.pottvine during the Fall '06 term at Indian Institute of Technology, Chennai.

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