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Q1_Wi06 - formalism Provide all proton transfer steps O H 2...

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NU, Winter 2006, Quiz 1, Chem 210-2 2 1. (20 pts) For a, gives the IUPAC names of the structure shown. For b-e, complete each of the following reactions by providing the missing starting materials, reagent set(s), or product (only the carbon-containing major product is necessary). If a reaction does not occur, please state so. Your answers should be consistent with any stereochemistry that the reaction may require. a. OMe b. Br O c. 1) O 3 excess 2) Me 2 S excess 3) LAH excess 4) Conc. H 2 SO 4 d. 1) KO t Bu, heat 2) CH 3 C(O)OOH 3) TsOH cat., HOCH 2 -CH 2 OH 4) conc. H 2 SO 4 O O e O O HO OH
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NU, Winter 2006, Quiz 1, Chem 210-2 3 2. (10 pts) Propose a mechanism for the following acid-catalyzed reaction using the curved arrow
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Unformatted text preview: formalism. Provide all proton transfer steps. O H 2 SO 4 cat., THF O NU, Winter 2006, Quiz 1, Chem 210-2 4 3. (20 pts). Propose a synthesis of the following compound from methane as the only carbon-containing starting material using only the reactions that you learned in Chem 210-1 and the last two weeks. You may use any necessary inorganic reagents, m CPBA, any alcohol protecting reagent, and any sulfur-containing reagent. Hint: If you don’t know how to start from methane, start from a known 2-C starting materials that could be made from methane… OH O...
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