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PS5(Ch21)_KEY - Problem Set 5 Chapter 21 1 Provide the...

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Problem Set 5: Chapter 21 1. Provide the products 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 N NH H + (cat) O OH HO O O H + Br 1. Ph 3 P 2. n -BuLi 3, acetaldehyde Cl O 1. (CH 3 ) 2 CuLi 2. H 3 O + O O NH 2 NH 2 KOH
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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 Cl O 1. ( ) 3 AlH 2. H 3 O + O H O H O BH 3 H 2 O OH O 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 ) 2 NH H 3 O + H + N H 2 O O N H H HO N H O H + (CH 3 ) 2 NH
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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. c. 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 + NO 2 H O O AlCl 3 Cl O O HNO 3 H 2 SO 4 O NO 2 1. NaBH 4 2. H 3 O + OH NO 2 POCl 3
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