Problem_Set_10_solutions - 3 CN AcOH N-Methylhexylamine...

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Chem 358 - Spring 2008 Problem Set 9 - Solution 1. NH H 2 N O O H OH N H 2 N O O H Br Br N H 2 N O O H Br OH N H 2 N O O Br N H 2 N O C O OH N H 2 N O C O OH HO H N H 2 N O C O O H H OH N H 2 N O H H OH N H 2 N O H H Base promoted hydrolysis of the amide N HO O H H N O H OH H N O H OH H N O H H OH N O H 2. O H 2 CO, NH 3 HCl (cat) O NH 2 1. CH 3 —Br (excess) 2. ! O 3. Write down the major organic product(s) of each of the following reactions. N 1. CH 3 I (excess) 2. Ag 2 O 3. ! NH O O 1. KOH 3. NaOH, H 2 O, ! O 2. NMe 3 HO ! Ph H CH 3 H 3 C H N 1. H 2 O 2 2. ! (a) (b) (c) (d) N CH 3 ONa ONa O O + H 2 N OH Ph H CH 3 H 3 C
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4. (a) 1. O 3 2. H 2 O 2 COOH COOH O COOMe COOMe 1. MeONa (1 equiv) 2. C H 3 Br O COOMe 1. NaOH, H 2 O, ! 2. H 3 O + , ! CH 2 N 2 (b) OOH O O OH NH 2 2. H 3 O + 1. NaNH 2 , H 2 O NH 2 (c) 1. NaNO 2 , HCl, 0°C 2. CuCN CN 1. LiAlH 4 , ether 2. H 2 O NH 2 OH O (d) 1. LiAlH 4 , ether N H OH 2. H 3 O + 1. PBr 3 2. CN CN 1. LiAlH 4 , ether 2. H 2 O NH 2 H 2 CO NaBH
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Unformatted text preview: 3 CN AcOH N-Methylhexylamine Reductive amination OH O (d) SOCl 2 , ether H N Cl 2. H 2 O H 2 CO, CH 3 NH 2 HCl (cat) O O O H N 1. (CH 3 ) 2 CuLi, ether 1. Zn[Hg], HCl 2. HO , H 2 O N-Methylheptylamine Mannich Reaction The two schemes labelled (d) and the scheme below in (e) illustrate how the different reactions lead to amines of different chain lengths. OH O (e) NH 3 (excess) ! NH 2 O NaOH, Br 2 , H 2 O ! NH 2 OH O (f) 1. SOCl 2 2. NaN 3 3. ! N C O MeOH N O Me O H...
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Problem_Set_10_solutions - 3 CN AcOH N-Methylhexylamine...

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