Problem_Set_5B_solution - SO 4 O 2 N Br 2 , FeBr 3 O 2 N Br...

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Chem 3580 - Spring 2009 Problem Set 5B - Solutions 1. (a) Retro analysis CH 2 COOH CH 2 CN CH 2 Br CH 2 OH Forward Synthesis CH 2 OH CH 2 Br CH 2 CN CH 2 COOH H 3 O + , ! PBr 3 KCN (b) NO 2 Br 2 FeBr 3 NO 2 Br (CH 3 ) 2 CuLi NO 2 CH 3 H 2 , Pd/C HN 2 CH 3 NaNO 2 , HCl 0°C N 2 Cl CH 3 CuCN CN CH 3 HCl, H 2 O ! COOH CH 3 SOCl 2 COCl CH 3 N H pyridine O N CH 3 (c) NH 2 O O O O NH O Na 2 Cr 2 O 7 , H 2 SO 4 ! NHAc COOH NH 2 COOH 1. HO , H 2 O, ! 2. Neutralize with acid ( 2 equiv) N COOH OH OH HCl, ! O N O HO " # PCl 3 or SOCl 2 O N O Cl " # O N O Cl " # N COOH Cl Cl 1. SOCl 2 2. H 2 O Base (K 2 CO 3 )
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(d) OCH 3 Br O OH O OH MgBr O Br MgBr Mg, ether 1. 2. H 3 O + O OH CrO 3 , H 2 SO 4 ! OH O OCH 3 O CH 2 N 2 or CH 3 OH, H 2 SO 4 , ! (e) F O OH O 2 N O OH O 2 N Br O 2 N CN O 2 N Gilman or Suzuki or Stille HNO 3 H 2
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Unformatted text preview: SO 4 O 2 N Br 2 , FeBr 3 O 2 N Br NC CuLi 2 O 2 N CN O 2 N O OH N 2 O OH N 2 O OH F O OH BF 4 HBF 4 ! Cl H + , H 2 O ! NaNO 2 , HCl, 0C H 2 , Pd/C H 2 N O OH 2. O + N H OH N ! H 2 N O N O HO N Br AlCl 3 HNO 3 , H 2 SO 4 O 2 N Na 2 Cr 2 O 7 , H + ! O 2 N OH O H 2 , Pd/C H 2 N OH O N OH O O O O O H SOCl 2 N Cl O O H Separate from the small amount of o-product formed...
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Problem_Set_5B_solution - SO 4 O 2 N Br 2 , FeBr 3 O 2 N Br...

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