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POD20Key - another Use the back of the page if you need...

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Problem of the Day #20 – Answer Key Deadline : 3:00 p.m., Friday, 8/15/08 LATE WORK WILL NOT BE ACCEPTED OR GRADED!!! This problem is worth 20 raw points. In each part below, propose a sequence of reactions to synthesize the target compound(s) 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. If a proposed reaction would produce products derived from substitution at the ortho and para positions, assume that these isomers can be separated from one
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Unformatted text preview: another. Use the back of the page if you need more space for your answers. and CH 3 OH (a) (8 points) Prepare (target) from as only sources of carbon atoms found in the target Br OCH 3 O CH 3 and (b) (12 points) Prepare (target, as a racemic mixture) from as only sources of carbon atoms found in the target N H OH Cl O Br OCH 3 O CH 3 H 2 CrO 4 , Δ OH O CH 3 OH H 2 SO 4 (cat.) OCH 3 O B r 2 F e 3 o A l ( c a t . ) (any suitable oxidizing agent) OH O Br Br 2 , FeBr 3 or AlBr 3 (cat.) CH 3 OH H 2 SO 4 (cat.) N H OH Cl O + AlCl 3 O HNO 3 + H 2 SO 4 Δ O O 2 N 1) Fe or Sn or Zn, HCl 2) NaOH, H 2 O O N H 2 Cl O (pyridine) O N H O 1) LiAlH 4 2) H 3 O + 3) NaOH, H 2 O...
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