Sampletest2KEY - O O O c. O HO CH 3 Cl AlCl 3 Cl O AlCl 3 O...

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SAMPLE TEST 2 1. Nomenclature: a. Acetophenone b. 2-phenylhexanenitrile c. 2-methylbutyl pentanoate O Cl N O O O H O Cl O Cl O CN Ph O O N,N-dimethyl-3-chloropentanamide butanoic 4-methylpentanoic anhydride 3-methylcycloheptane carbaldehyde 2-chloro-3-methylbutanoyl chloride
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2. Reactions OH 1. PCC 2. NH 2 NH 2 , KOH, heat H O OH Ag 2 O NH 4 OH, H 2 O OH H + O OCH 3 1. DIBAL, -78 o C 2. H 3 O + CH 3 NH 2 H + O OH 1. SOCl 2 2. NH 3 (2 eq.) SOCl 2 O Br OH O OH O OH O O OH Ph O H N H CH 3 O NH 2 C N 1. O 3 , -78 o C 2. Zn, CH 3 CO 2 H H 2 C PPh 3 1.NaCN, 2. H 3 O + OR 1. Mg, ether 2. CO 2 3. H 3 O +
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O 1. (CH 3 ) 2 CuLi 2. H 3 O + 3. (CH 3 ) 2 NH, H + C N 1. PhMgBr 2. H 3 O + HOCH 2 CH 2 OH H + Br PPh 3 O 1. CH 3 MgBr 2. H 3 O + CH 3 NH 2 N H 3 C CH 3 Ph Ph O O O Ph Ph 1. Ph 3 P 2. n-butyl lithium PhCHO OH H 3 C O N H
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3. Provide the mechanism for the following reaction O NH 2 O OH + NH 4 H 3 O + H + O NH 2 H H 2 O OH NH 2 O H H OH NH 3 O H O OH H + NH 3
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4. Synthesis: a. H 2 N O b. OH
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Unformatted text preview: O O O c. O HO CH 3 Cl AlCl 3 Cl O AlCl 3 O 1. NaBH 4 2. H 3 O + HO 1. PBr 3 2. NaCN NC H 3 O + HO O 1. SOCl 2 2. NH 3 (2 eq.) CH 3 OH H + O O CH 3 O O 1. DIBAL, -78 o C 2. H + H O O O H CH 2 O O H 3 O + H 2 C PPh 3 1. NaBH 4 2. H 3 O + OH SOCl 2 Cl 1. NaCN 2. CH 3 MgBr 3. H 3 O + O 1. NaBH 4 2. H 3 O + 5. NMR Molecular Formula: C 12 H 16 O 2 IR: 1730 cm-1 1H NMR: 0.9 ppm, triplet, 3H 1.2 ppm, doublet, 3H 1.8 ppm, quintet, 2H 3.5 ppm, singlet, 2H 4.0 ppm, sextet, 1H 7.4-7.8 ppm, multiplet, 5H O O a b c d e f f d e c a b...
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This note was uploaded on 03/29/2008 for the course CEM 251 taught by Professor Rathke during the Spring '07 term at Michigan State University.

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Sampletest2KEY - O O O c. O HO CH 3 Cl AlCl 3 Cl O AlCl 3 O...

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