SynthesisQuiz - KMnO 4 H C C H H 3 C C C CH 2 CH 3 H C C H...

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Name ________________________ Page 9 V. (30 points) Using ONLY the reagents listed on the side, design your own synthesis of the racemic mixture of diols shown below: H 2 (gas) Pd/BaSO 4 quinoline NOTE: mechanistic steps (curved arrows) should n o t be shown. Simply provide the reactants and products of the reactions needed to accomplish this synthesis. You will be graded on conceptual correctness as well as the validity of the reactions you choose. Be sure to show stereochemistry when appropriate.
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Unformatted text preview: KMnO 4 H C C H H 3 C C C CH 2 CH 3 H C C H H H CH 3 CH 2 CH 2 Br CH 3 CH 2 CH 2 CH 2 CH 2 Br CH 3 CH 2 CH 2 CH 2 Br CH 3 CH 2 Br CH 3 Br H 3 CH 2 CH 2 C C C HO CH 2 CH 3 OH H H H 3 CH 2 CH 2 C C C H OH CH 2 CH 3 HO H H 3 O + C O O O H Cl Reagent Shelf 30 Br 2 BH 3 NaOH HBr NaNH 2 H 2 O 2 H 2 O Pt Na NH 3...
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