Problem_Set_3_KEY - Problem Set #3: Chapters 19 1. Provide...

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Problem Set #3: Chapters 19 1. Provide the products and/or the conditions for the following transformations: OCH 3 OCH 3 1. H 3 O + 2. Ph 3 P CH 2 H O CH 3 NH 2 H + (cat) H N O 1. (CH 3 ) 2 CuLi 2. H 3 O + O 1. CH 3 MgBr 2. H3O + OH O N NH H + (cat) O OH HO O O H +
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Br 1. Ph 3 P 2. n -BuLi 3, acetaldehyde O H N O N H H O O O OH H + H 1. O 3 2. Zn / CH 3 COOH H O O H 3 O + HgSO 4 O O O H O or 1. DIBALH, -78 o C 2. H 3 O + 1. DIBALH, 2. H 3 O + 3. PCC
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2. Provide a detailed reaction mechanism for the following transformations: a. b. H 3 CO OCH 3 H 3 O + O + CH 3 OH O H H H H 3 CO OCH 3 H O H 2 O HO OCH 3 HO OCH 3 H H + H O + CH 3 OH H N O + CH 3 NH 2 H 3 O + O H H H N H H 2 O O NHCH 3 H H HO NHCH 3 H O H + CH 3 NH 2
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3. Provide a reasonable synthesis for the following molecules using the given starting material and any other carbon contaning compound you need with 2C atoms or less. a. b. H OH H O O HO OH H + H OH O O CrO 3 , H 2 SO 4 , H 2 O H O O O PPh 3 H 3 CHC H O O H + O 1. (CH 3 CH 2 ) 2 CuLi 2. H 3 O + O Si(CH 3 ) 3 O 1. NaBH 4 2. H 3 O + OH (CH 3 ) 3 SiCl (CH 3 CH 2 ) 3 N
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c. d.
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Problem_Set_3_KEY - Problem Set #3: Chapters 19 1. Provide...

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