CHEM 343 Problem Set 3 Key O O 1 H work up NHMe O 2 2 1 LAH O O Cl N Me NHMe O Br 1 NaOEt then Br O 2 NaOEt Br O O 3 NaOH I 2 H O work up O O 4 OH Li 3 N 1 MgBr O 2 LDA 78o EtBr or H work up H work up O O 3 mCPBA O 4 O 1 MeONa R T then Cl2 O Cl Cl O 5 O O 2 NH 2OH H another product is also formed O 2 Et 2CuLi then Br 2 1 MeONa then H work up 6 O N H LDA 78o then O H work up O O Br 7 HO 8 H O H H 2O work up H SEt O O 2 LDA 78o then O 3 EtSH 1 DIBAL H work up N H O 2 MeMgBr 1 equiv O 1 SOCl2 pyridine Cl H work up O OH 9 O O 1 NaOEt O OEt 2 NaOEt 1 3 dibromopropane O O OEt 3 H H 2O OEt O 10 O O 1 NaOH H work up OH O 3 LAH NEt 2 NEt 2 O O 11a O 2 DCC NHEt 2 O O 1 H H 2O HO 2 OH O 3 MeOH HO O Cl OMe 11b Propose anoither method to complete the same transformation O O H MeOH O HO OMe HO O O 12 O O 1 LAH 0 25 equiv H work up O 2 LDA 78o H work up H Cl O O O 3 Me 2CuLi then MeBr O 13 racemic O 1 H H 2O NH 2 2 LAH H work up OH OH O 3 H OH O O mol sieves 14 Propose a mechansim for the following reaction O O LDA 78o H work up O O O O O O O 2H H O OH2 Li NR 2 H O O 14 Propose a mechanism for the following sequence N O Base then OPh O O O N N Hint 1 the nitrogen in the starting material is a good electrophile Hint 2 a molecule of CO 2 is formed O O OPh OPh H O Base N OPh O O N OPh N O O O O N N
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