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Problem of the Day #17 – Answer Key Deadline : 3:00 p.m., Tuesday, 8/12/08 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. [Note : You may use other carbon- containing reagents, as long as they do not contribute carbon atoms to the final target molecule.] 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. OH and CH 3 CH 2 Br O (a) (10 points) Prepare (target, as a mixture of stereoisomers) from as only sources of carbon atoms found in the target (b) (1 points) Prepare (target) from as only sources of carbon atoms found in the target OH O and EtO OEt O O O and (CH 3 ) 2 CuLi 4 Li 2 CuCl + LiCl 1) (CH 3 CH 2 ) 2 CuLi 2) dil. H 3 O + + LiBr NaBH 4 in CH 3 OH OR 1) LiAlH 4 2) H 3 O + (racemic) CH 3 CH 2 Br O Br 2 in CH 3 CO 2 H O Br KO t Bu in t BuOH O O (mixture of stereoisomers) OH (racemic) 2 CH 3 CH 2 Li (CH 3 CH 2 ) 2 CuLi + EtO OEt O O NaOEt, EtOH, Δ EtO OEt O O O 1) (CH 3 ) 2 CuLi 2) dil. H 3 O + EtO OEt O O 2) 1) NaOH, H 2 O H 3 O + , Δ OH O...
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