ExamF07.3ans - 3(20 points Which product would be formed...

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3. (20 points) Fill in the missing starting material, reagent or product. a. b. c. Name ___________________ d. 1. (20 points) Deduce the structure of B , and fill in the missing reagent(s). You do not need to show mechanisms. This is an open-book, open notes exam. Please show your work in detail. Exam #3 Friday, November 16, 2007 Chem 331 ? NaBH 4 OH Br ? CN MgBr H 3 C N H 3 C O H ? O ? O C 7 H 12 O (then work up) O O OH ? 1 H NMR: 9.80 dd, 1H, J = 1.2, 2.0 4.55 tt, 1H, J = 6.0, 6.8 4.18 dd, 1H, J = 6.0; 8.4 3.58 dd, 1H, J = 6.8, 8.4 2.85 ddd, 1H, J = 2.0, 6.8, 17.2 2.65 ddd, 1H, J = 1.2, 6.0, 17.2 1.41 s, 3H 1.36 s, 3H A B C 7 H 12 O 3 13 C NMR: 200.0, d 109.2, s 70.6, d 69.1, t 47.8, t 26.8, q 25.4, q CrO 3 O O O H O H H 2 C CN H 2 Pd cat O H
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4. (20 points) Deduce the stucture of D , and draw an arrow-pushing mechanism for the transformation.
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Unformatted text preview: 3. (20 points) Which product would be formed, and why? 1 H NMR: 9.48 s, 1H 6.19 s, 1H 5.93 s, 1H 2.18 t, 2H, J = 7.6 Hz 1.2-1.5 br m, 8 H 0.87 t, 3 H, = 7.0 Hz 13 C NMR: 194.6, d 150.4, s 133.7, t 31.5, t 28.8, t 27.7, t 27.6, t 22.4, t 13.9, q H O O O D C 9 H 16 O C O MgCl HO HO HO HO HO HO HO HO O OH S S I S = same I= inverted O H O O H H O OH O + D 5. (20 points) Draw a detailed arrow-pushing mechanism for the transformation of E to F . O Br Bu 3 SnH AIBN a b c d e f g O E F bb bf Sn-H g-Br Sn-Br e-H h-e h-g R H SnBu 3 O Br SnBu 3 O + Bu 3 SnBr O O H SnBu 3 O + SnBu 3 h g e f...
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This note was uploaded on 07/08/2008 for the course CHEM 331 taught by Professor Kramer during the Spring '08 term at University of Delaware.

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ExamF07.3ans - 3(20 points Which product would be formed...

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