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04_15_2008_problem_session_key

04_15_2008_problem_session_key - Cl Br N CH 3 H 3 C OH OH...

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Tuesday Problem Session - 15 April 2008 1 H 3 O + 1. LiAlH 4 2. H 3 O + OCH 3 O O CH 3 OH, H + OH O O OCH 3 O (excess) CH 3 O CH 3 O OH O Br O SOCl 2 Cl O O NHCH 3 O O NaCN CN O N N 1. LiAlH 4 2. H 3 O + NHCH 3 HO H 2 / Ni H O O CH 3 CH 3 CH 3 CH 3 OCH 3 O O CH 3 OH NaBH 4 , CH 3 OH OCH 3 O HO COOH O H 3 O + OCH 3 O O PCC PBr 3 HN PCl 3 or H 2 NCH 3 CH 3 CH 3
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2 Circle the isoprene structural units in: isoprene myrcene CH 3 OH menthol β -pinene Make SYNTHESES From OCH 3 O OH OH Br OCH 3 O Br 2 FeBr 3 1. Mg 2. CO 2 3. H 3 O + CH 3 OH, H + Br PBr 3 1. Mg 2. H 2 CO 3. H 3 O + One solution shown for each problem, many others are possible
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