Problem_Set_2 - A C 6 H 14 O 3.5 3.0 2.5 2.0 1.5 1.0 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0

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Problem Set #2: Chapters 17, 18 1. Provide the products and/or the conditions for the following transformations: O 1. NaBH 4 2. H 3 O + 3. SOCl 2 O O 1. CH 3 MgBr (2 eq) 2. H 3 O + 3. POCl 3 , pyr OH OH O HO 1. LiAlH4 2. H 3 O + 3. PBr 3 Ph O Ph OH
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OH 1. SOCl 2 2. Mg, ether 3. 4. H 3 O + O O O O 1. LiAlH 4 2. H 3 O + 3. PCC O Ph Ph OTMS 1. CH 3 CH 2 MgCl 2. H 3 O + 3. PCC O H
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2. 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. OH O (KSO 3 ) 2 NO OH OH O H O OH OH O
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HO H O O O H Br O HO OH O O OH OH HO H O O
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4. Determine the structure of the following compounds based on their 1H-NMR spectra:
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Unformatted text preview: A. C 6 H 14 O 3.5 3.0 2.5 2.0 1.5 1.0 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0 11.5 12.0 12.5 13.0 13.5 14.0 14.5 15.0 15.5 16.0 16.5 1H-NMR: 0.89 ppm (d, 6H); 1.15 ppm (t, 3H); 1.6 (multiplet, 1H); 3.20 ppm (d, 2H); 3.55 ppm (q, 2H) 6 3 1 2 2 B. C 14 H 22 O 1H-NMR: 0.90 ppm (t, 6H); 1.18 ppm (d, 3H); 1.69 ppm (d, 2H); 3.58 ppm (s, 1H); 4.03 ppm (multiplet, 1H); 7.20-7.5 ppm (multiplet, 5H) 1 2 3 4 5 6 7 8 PPM...
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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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Problem_Set_2 - A C 6 H 14 O 3.5 3.0 2.5 2.0 1.5 1.0 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 4.0 4.5 5.0 5.5 6.0 6.5 7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.0

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