ExamF07.2ans - D , you may use any piece that contributes...

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This is an open-book, open notes exam. Please show your work in detail. 1. (20 points) Draw the structures of B and C , and give IUPAC names for A , B , and C . You do not have to show mechanisms, but you do need to show stereochemistry clearly. Chem 331 Exam #2 Friday, October 19, 2007 Name ___________________ 2. (20 points) Indicate the expected major product. Explain your reasoning in detail. O A B C 7 H 13 Br C C 9 H 16 O Mg; CH 3 CN OH PBr 3 O O O O O O O Br Br 1. ONa O 2. KOH key Br O O O O Br O benzylic Br more reactive HO O Br O same inverted inverted (1S, 3S)-3-methylcyclohexanol (1R, 3S)-1-bromo-3-methylcyclohexane 1-((1R, 3S)-3-methylcyclohexyl)ethanone
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13 C NMR 14.6, q 53.0, d 127.5, d 128.3, d (2) 129.0, d (2) 137.8, s 200.8, d 4. (20 points) Deduce the stucture of F , and draw an arrow-pushing mechanism for the transformation. 3. (20 points) Outline the synthesis steps to convert D into E . In addition to
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Unformatted text preview: D , you may use any piece that contributes three or fewer carbons to the final product. 1 H NMR 1.42, d, J = 7.3 Hz, 3H 3.63, dq, J = 4.2, 7.3 Hz, 1H 7.22, dd, J = 8.1, 2.4 Hz, 2H 7.31, dd, J = 8.1, 8.2 Hz, 2H 7.38, td, J = 8.2, 2.4 Hz, 1 H 9.65, d, J = 4.2 Hz, 1H D HO O H + O F C 9 H 10 O TsCl, pyridine TsO MgCl MCPBA O CH 3 MgBr OH CrO 3 H + CH 3 O H H OH CH 3 H O H 3 C H H O H 3 C F 5. (20 points) Draw a detailed arrow-pushing mechanism for the following transformation. 5/20 points for correctly showing the mapping of the starting material onto the product. O O CO 2 CH 3 + S O O O CO 2 CH 3 bb bf a b c d e f f a b c d e O-e a-d f-H f-S a-f e-f O-f d-H S O f O O CO 2 CH 3 S O O CO 2 CH 3 S O O O CO 2 CH 3 S O O CO 2 CH 3 S O O H + transfer O O CO 2 CH 3 O S O + S O DMSO...
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ExamF07.2ans - D , you may use any piece that contributes...

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