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HW20Key - mechanisms for the reactions that you use Use the...

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Graded Homework Problem #20 – Answer Key Deadline : 3:00 p.m., Thursday, 5/1/08 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 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. (a) Prepare from (b) Prepare from OH (racemic) Cl Br 2 , h ν Br (radical chlorination is also acceptable) KO t Bu in t BuOH [E2] (other strong bases are acceptable for both E2 rxns) NBS h ν or Δ Br (racemic) (allylic bromination) KO t Bu in t BuOH [E2] OH (racemic) Cl conc. H 2 SO 4 Δ 1) BH 3 2) H 2 O 2 , NaOH, H 2 O OH SOCl 2 in pyridine OR HCl (conversion of alcohol to alkyl halide followed by E2 is also acceptable)...
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