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POD08Key - Use the back of the page if you need more space...

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Problem of the Day #08 Answer Key Deadline : IN CLASS on Th 7/22/2010 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth a total of 20 raw points. In each part below, propose a sequence of reactions to synthesize the target compound from the indicated starting material(s). You may use any other organic and/or inorganic reagents necessary to complete your synthesis, but all carbon atoms in the target must be derived from the starting material(s) specified in each part. It is only necessary to give overall transformations in answering this question. It is not necessary to provide complete curved arrow mechanisms for the reactions that you use.
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Unformatted text preview: Use the back of the page if you need more space for your answers. (b) (12 points) Prepare (target) from as only source of carbon atoms O CH 2 OH (a) (8 points) Prepare (target) from and CH 3 CH 2 Br and CH 3 OH as only sources of carbon atoms H 3 CO OCH 3 (target) H 3 CO OCH 3 1) NaNH 2 2) CH 3 CH 2 Br HgSO 4 , H 2 SO 4 , H 2 O OR 1) (sia) 2 BH or BH 3 2) H 2 O 2 , NaOH, H 2 O O CH 3 OH, H 2 SO 4 (cat.) CH 2 OH HBr or PBr 3 [HCl or SOCl 2 , pyridine] CH 2 Br[Cl] Mg, ether CH 2 MgBr[Cl] (= BnMgX) CH 2 OH PCC H O 1) BnMgX (from above) 2) H 3 O + OH (racemic) O H 2 CrO 4...
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