02 - MgBr Na racemic H O racemic racemic racemic racemic Ph...

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OH OH OH OH OH OH OH OH Br O O O H O O Br OH O O OH O O OH OH OH 2 H O Ph O OMe O CH 3 O CH 3 O OH O OH Ph OH HO I Br Cl Br O OTs H OH O O OH OH OH OH + OH OH 1 . Provide products for the following reactions OH HI OH Ph HBr SOCl 2 PBr 3 NaH ether Ph OH TsCl pyridine PCC H 2 CrO 4 OH a) O b) c) OH d) Ph OH e) f) g) h) O 1.LiAlH 4 2. H 3 O + O S O OH O 1. NaOH 2. H 2 SO 4 , H 2 O H 2 SO 4 , H 2 O 1. NaBH 4 2. H 3 O + H 2 SO 4 , H 2 O H 1. CH 3 MgBr 2. H 3 O + 1. CH 3 MgBr 2. H 3 O + OH 2 H i) j) k) l) Ph OH m) O S O OH O 1. Mg 2. PhCHO 3. H 3 O + 1. PhMgBr 2. H 3 O + o) n) H H 2 SO 4 , H 2 O H PCC H 1.LiAlH 4 2. H 3 O + OH 2 1. H 2 SO 4 , H 2 O 2. CrO 3, pyridine 3. PhMgBr 4. H 3 O + p) H q) OH r) H B H H H s) t) u) 2. Show detailed mechanisms for the following reactions. H CH 3 Cl Ph OH H CH 3 H Cl H 3 O a) b) Cl c) OMe O CH 3 d) e) f) g) CH 3 O h) 3. a) HO b) c) d) OH + H O Chem 212 Alcohol Problems 2 ANSWERS page 1
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Unformatted text preview: MgBr Na racemic H O racemic racemic racemic racemic Ph H O H 3 O H 3 O Ph MgBr H 2 O CH 3 H O H 3 O [-OMe] O H 3 O + MeMgBr O + + EtMgBr MgBr O O MgBr OMe O + + EtMgBr + MeMgBr + MgBr 2x H 4 O H 2 O OH OH OH OH O MgBr O H MgBr O H f) g) O h) e) Chem 212 Alcohol Problems 2 ANSWERS page 2 EtMgBr + O H + CH 2 O + EtMgBr MgBr + + MeMgBr O H MgBr + H 2 SO 4 , H 2 O + +...
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