07FH9ans - 77.8, d 80.1, d 113.6, d (2) 128.3, d (2) 132.6,...

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3. Outline a synthetic route to D . Show all reagents. You may use any starting material that incorporates three or fewer carbons in the final product. Absolute configuration does not matter, but you must show how to control relative configuration. 1. (10 points) Deduce the structure of B , and draw an arrow-pushing mechanism for the transformation. Stereochemistry is important! 2. (10 points) Draw an arrow-pushing mechanism for the following transformation: Fall 2007 Homework #9 due: 10 a.m. Monday, November 12th Name ___________________ Chem 331 13 C NMR: 15.5, q 15.6, q 55.2, q 64.4, t
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Unformatted text preview: 77.8, d 80.1, d 113.6, d (2) 128.3, d (2) 132.6, s 159.2, s 1 H NMR: 0.97, d, J= 6.1 Hz, 3H 1.26, t, J= 7.0 Hz, 3H 3.5, m, 2H 3.71, dq, J = 9.3, 6.1 Hz, 1H 3.80, s, 3H 4.33, d, J = 9.3 Hz, 1H 6.90, d, J =8.1 Hz, 2H 7.28, d, J =8.1 Hz, 2H HO C 12 H 18 O 3 D H + O CH 3 CH 2 OH K 2 CO 3 B CH 3 O O O OCH 3 O CH 3 O OH key O H O O O O-CH 2-CH 3 CH 3 O HO O CH 3 O O OH does not fit the data as well - note the calculated 13 C chemical shifts 85 84 14 95 71 17 OH O OCH 3 O CH 3 O O H H O CH 3 O O H H O CH 3 O O CH 3 O H O H PPh 3 MCPBA O MgCl HO BH 3 ; ox HO D OH...
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