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Unformatted text preview: O H O Mn O NaOH/H 2 O O H 1 2 O 3 6 O Mn O O Mn O O H H HO OH H 2 + H 2 O + Mn O O O Mn O O H H O H 2 + Mn OH O or +4 +4 +2 need not to show mech. arrows: 1 pt mech. arrows: 2 pt interm. str.: 2 pt Mn (+2): 1 pt Br OH OH Br OH Br H H H Note: 3D bridge structure NaH NaH NaH (1) (2) (3) 2 2 2 Br OH OH Br H H O H NR NR Chem 215-216 HH W10 Quiz 6 page 2 III . (8 points) Complete each of the following reactions by drawing the structure of the expected major product in the box. Make sure to clearly indicate the stereochemistry whenever applicable. 2 O H 3 C D D 3 C H O H 3 C D D 3 C H 2 tetrahrdrofuran (solvent) 0 C, 1 h HClO 4-H 2 O CH 3 ONa-CH 3 OH reflux, 2 h 2 2 tetrahrdrofuran (solvent) 0 C, 1 h HClO 4-H 2 O H O tetrahrdrofuran (solvent) 0 C, 1 h HClO 4-H 2 O H O OH H 3 C D D 3 C H OH OH H 3 C D D 3 C H OCH 3 H HO HO H HO HO diaxial opening of the epoxide ring...
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This note was uploaded on 02/24/2010 for the course CHEM 215 taught by Professor Koreeda during the Spring '07 term at University of Michigan.
- Spring '07