07FH11ans - Name ___________________ Chem 331 13 C NMR:...

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3. Outline a synthetic route to E . 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 fill in the missing reagent(s). 2. (10 points) Draw an arrow-pushing mechanism for the following transformation: Fall 2007 Homework #11 due: 10 a.m. Monday, December 3
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Unformatted text preview: Name ___________________ Chem 331 13 C NMR: 20.6, q 56.6, q 109.2, d 122.1, d 123.6, d 131.6, s 138.7, s 157.4, s 173.1, s 1 H NMR : 2.45 s, 3H 3.88 s, 3H 6.82 d, 1H, J = 8.0 Hz 6.83 d, 1H, J = 8.0 Hz 7.29 t, 1H, J = J = 8.0 Hz C 9 H 10 O 3 A E C D B H + CN OH O OH OH OH CH 3 O CO 2 CH 3 CH 3 O CO 2 H NaOH H + O OH H OH OH OH OH H Br Br MgCl Br NaCN DMSO CN MCPBA CN O CN OH LDA LDA x 2; Br CN OH...
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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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