07FH8ans - 34.5, d 166.8, s 60.1, t 63.5, t (2) 1 H NMR:...

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3. Outline a synthetic route from E to F . Show all reagents. 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. 2. (10 points) Draw an arrow-pushing mechanism for the following transformation: Fall 2007 Homework #8 due: 10 a.m. Monday, November 5th Name ___________________ Chem 331 13 C NMR: 14.2, q 97.9, s 23.4, q 121.6, d 24.4, q 147.0, d
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Unformatted text preview: 34.5, d 166.8, s 60.1, t 63.5, t (2) 1 H NMR: 1.27, t, J = 7.1 Hz, 3H 1,39, s, 3H 1.42, s, 3H 3.6, m, 1H 3.71, dd, J =5.9, 11.6 Hz, 2H 4.06, dd, J =4.0, 11.6 Hz, 2H 4.15, q, J = 7.1 Hz, 2H 5.89, d, J =5.9, 11.5 Hz, 1H 6.41, dd, J =9.5, 11.5 Hz, 1H O OCH 3 C 11 H 18 O 4 B E OH O H 2 C N N CN F C D O O CO 2 Et OH H + A H + O O CO 2 Et O H H H O O CO 2 Et Could be Z or E- from J = 11.5 must be Z O-H O H 2 C N N O O H 3 C N N + N 2 MCPBA O CH 3 MgBr OH PBr 3 Br CH 2-CN...
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