PS2(Ch17_18) - 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 0.0 0.5...

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Problem Set 2: Chapters 17, 18 1. Provide the products of the following transformations HNO 3 H 2 SO 4 H 2 , Pd CH 3 Cl, AlCl 3 Br 2 FeBr 3 NBS H 2 O 2 AlCl 3 Cl H 2 , Pd AlCl 3 Cl O H 2 SO 4 heat
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KMnO 4 NaOH heat I 2 CuCl 2 AlCl 3 Cl H 2 SO 4 heat 1. NaOH 2. H 3 O + HNO 3 H 2 SO 4 Cl AlCl 3 Sn HCl
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2. Provide the conditions for the following transformations: NO 2 NO 2 NH 2 Cl OH OH +
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3. Determine where a 3 rd electrophile would add to the following benzenes: 4. Provide a synthesis for the following molecules starting from benzene (you need to go through several steps and/or use some reactions from CEM251): NH 2 NO 2 SO 3 H HO OH Cl NO 2 O 2 N NH 2 Cl
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NO 2 O CO 2 H Br
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4. Determine the structure of the following compounds based on their 1H-NMR spectra: A. C 8 H 10 O 6.5
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Unformatted text preview: 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 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 2.24 ppm (s, 6H); 5.00 ppm (s, 1H); 6.33 ppm (s, 2H); 6.58 ppm (s, 1H) 1 6 2 1 B. C 10 H 14 7.0 6.5 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 1.5 1.0 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 3 3 2 2 2 2 Expansion: 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 NMR: 0.93 (t, 3H); 1.64 (sextet, 2H); 2.27 (s, 3H); 2.59 (t, 2H); 6.77 (d, 2H); 6.91 (d, 2H)...
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PS2(Ch17_18) - 6.0 5.5 5.0 4.5 4.0 3.5 3.0 2.5 2.0 0.0 0.5...

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