POD07Key - mechanisms for the reactions that you use Use...

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CH s310N/s318N Summer 2008 Last Name: First Name: Dr. Bocknack UTEID: Score: Problem of the Day #07 Deadline : 3:00 p.m., Wednesday, 7/23/08 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
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Unformatted text preview: mechanisms for the reactions that you use. 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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