Friday_Session_4_solution - Chem 358 Spring 2009 Friday...

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Chem 358 – Spring 2009 Friday Session #4 – Feb 20, 2009 Cl OH Cl O O NaH 1. NaCN CN OH 2. H 3 O + HCl, H 2 O ! COOH OH ———————————————————————————————————— Cl OH CN OH HCl, H 2 O COOH OH NaCN ! Br 1. Mg, ether 2. CO 2 3. H 3 O + OH O SOCl 2 Cl O CoLi 2 O C C Li OH 1. 2. H 3 O + Think of other possibilities and try them. ———————————————————————————————————— Cl AlCl 3 NO 2 1. KMnO 4 , HO H 3 O + COOH NO 2 2. HO , H 2 O 1. Fe, HCl COOH NH 2 HNO 3 H 2 SO 4 ———————————————————————————————————— Br 2 FeBr 3 Br B O O Pd(PPh 3 ) 4 K 2 CO 3 NC CN HCl H 2 O, ! COOH COCl 1. AlCl 3 2. H 2 O O 1. LIAlH 4 or NaBH 4 2. H 3 O + OH SOCl 2 H 2 SO 4 ! 1. PBr 3 2. tBuO - ———————————————————————————————————— O O O AlCl 3 O OH O Zn[Hg] HCl OH O SOCl 2 Cl O O 1. AlCl 3 2. H
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Friday_Session_4_solution - Chem 358 Spring 2009 Friday...

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