CHEM 343 Problem Set 2 Key 1 NO 2 Br 1 Br 2 FeBr 3 NO 2 H 2N 3 H2SO 4 excess Br Br NH 2 NH 2 SO 3H 2 Br 2 H 2 Pd C X 1 X2 AlCl3 SO 3H Cl 3 Cl2 2 NaNH 2 Cl O O 3 O 2 HNO 3 H 2SO 4 AlCl3 1 Cl sole product NO 2 3 H 2NNH 2 KOH or HCl Zn Hg NO 2 O 4 O Cl H Br 1 O AlCl3 H 2 Mg 0 H work up O Br para product O O MgBr H 3 H 2NNH 2 KOH or HCl Zn Hg O OH OH para product would only give intermolecular reaction O 5 O H OH 3 MeLi or MeMgBr O O OTBS H 6 O H work up OTBS O H work up 5 TBAF OH 1 H H 2O OH O HO OTBS Note steps 1 and 2 could be reversed as could steps 4 and 5 OH O 2 or H OEt 4 H H 2O O OH H O OEt 2 TBSCl imidazole O 1 equiv O O O O OH 1 H HO Li O MgBr 1 equiv H work up NMe OH 3 H trace NH 2Me 7 1 Cl 2 Cl2 AlCl3 AlCl3 Cl 3 H 2SO 4 excess HO 3S Cl 8 Cl 1 AlCl3 3 KMnO 4 HO O 2 Cl AlCl3 OH 9 NO 2 1 H 2SO 4 HNO 3 N 10 N 3 HONO HCl N O Cl Br 5 Br 2 FeBr 3 4 CuCN 1 O NH 2 2 H 2 Pd C AlCl3 O O H 2 NaBH 4 H work up H OH N OH 3 Cl2 AlCl3 OH OH Cl 11 O O O H OH O OH 2 Br 2 FeBr 3 1 MeMgBr 1 equiv H work up Br 3 Li O O then H OH H H work up HO O 12 O H O O 1 Ph 3P O O O 3 H H 2O H OH O O 2 NaBH 4 H work up O OH 13 Using the starting material shown below and anything else you might need synthesize the desired product O O starting material OH product O O O 2 KMnO 4 1 MeCl AlCl3 3 MeCl AlCl3 O OH O 4 H 2NNH 2 KOH heat or HCl Zn Hg O OH O OH 14 Using the starting material shown below and anything else you might need synthesize the desired product Cl NH 2 product starting material Cl 1 NaNH 2 2 H 2 Pd C 3 H 2 Pd C NH 2 3 HNO 3 H 2SO 4 NO 2 15 Show the mechanisms for the formation of both A and B O H 2SO 4 Cl AlCl3 A OH OH OH2 H H O O Cl AlCl3 Cl O AlCl3 H O A O B B
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