ExamF07.4ans - 32.7 d 21.2 q F C 9 H 16 O 2 E O O MgCl 3(20...

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2. (20 points) Fill in the missing starting material, reagent or product. a. b. c. Name ___ k e y_____________ d. This is an open-book, open notes exam. Please show your work in detail. Exam #4 Friday, December 14, 2007 Chem 331 ? O ? ? H 2 Pd cat poioned H OH OH H 2 N NH 2 NaH H ? O 1. (20 points) Deduce the structure of B , and fill in the missing reagent(s). You do not need to show mechanisms. 1 H NMR: 5.56, ddd, J = 15.2, 6.8, 5.1 Hz, 1H 5.34, ddd, J= 15.2, 7.2, 5.2, Hz, 1H 3.73, s, 6H 3.41, t, J = 7.6 Hz, 1H 2.58, m. 2H 1.9 - 2.1, m, 2H 0.94, t, J = 7.1 Hz, 3H B C 10 H 16 O 4 13 C NMR: 169.2, s (2) 135.5, d 123.9, d 52.4, q (2) 52.0,d 31.9, t 25.6, t 13.8, q A CO 2 CH 3 CO 2 CH 3 Br CO 2 CH 3 CO 2 CH 3 H Bu 3 SnH AIBN MgCl OH H H 2 SO 4 Hg cat
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4. (20 points) Deduce the structure of F , and draw an arrow-pushing mechanism for the transformation. 1 H NMR: 6.26 d, J = 12.9 Hz, 1H 5.84-5.69 m, 1H 5.04-4.95 m, 2H 4.73 dd, J = 12.9, 8.4 Hz, 1H 3.85-3.73 m, 4H 2.2 bs, 1H (exchanges) 1.9 - 2.1 m, 3H 1.00 d, J = 6.6 Hz, 3H 13 C NMR: 144.9, d 137.1, d 115.7, t 110.6, d 70.1, t 61.4, t 42.3, t
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Unformatted text preview: 32.7, d 21.2, q F C 9 H 16 O 2 E O O MgCl 3. (20 points) Outline a synthesis of D from C . You may use any piece that contributes three or fewer carbons to the final product. Absolute configuration is not important, but relative configuration is. CH 3 O Br C CH 3 O D OH H 3 C H BuLi; I H 3 C H 2 Pd cat poisoned H 3 C MCPBA H 3 C O CH 3 O Br Mg; H 3 C O CH 3 O OH O HO Note the CH 3 doublet at 1.00 The alkene couplings and chemical shift are also diagnostic 5. (20 points) Draw a detailed arrow-pushing mechanism for the transformation of G to H . 5 points for correctly labelling H . Cs 2 CO 3 cat Ph 3 P G H bb bf CO 2 CH 3 Br CO 2 CH 3 a b c d e f g h CO 2 CH 3 CO 2 CH 3 a b c d e f g h a-b f-g h-Br a-h b-f g-h CO 2 CH 3 Br CO 2 CH 3 Ph 3 P CO 2 CH 3 PPh 3 CO 2 CH 3 Br H O O O CO 2 CH 3 PPh 3 CO 2 CH 3 CO 2 CH 3 CO 2 CH 3 PPh 3 CO 2 CH 3 CO 2 CH 3 PPh 3 CO 2 CH 3 CO 2 CH 3 + Ph 3 P (catalytic)...
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ExamF07.4ans - 32.7 d 21.2 q F C 9 H 16 O 2 E O O MgCl 3(20...

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