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Bocknack CH 310M/318M Fall 2009 Graded Homework Problem #20 – Answer Key Deadline : 3:00 p.m., Thursday, 12/3/09 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. In each part, you should only need to use reactions that we studied in Chapters 6 through 9!!! Prepare from as the only sources of C atoms in the target (b) (12 points) C N and KCN Hint : The benzylic position of ethylbenzene is comparable in reactivity to the allylic position of an alkene. (benzylic position) TARGET Prepare from as the only source of C atoms in the target (a) (8 points) CH 3 H CH 3 O O TARGET Br 2 , h ν C N NBS, h ν OR Br KO t Bu in t BuOH (E2) HBr, peroxides Br KCN (S N 2) (any strong base OK) Br 2 , h ν CH 3 H CH 3 O O H 3 C Br NaOEt in EtOH (E2) (any strong base OK) CH 3 1) O 3 2) (CH 3 ) 2 S...
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