E3,241b,S06 - EXAM 3 CHEMISTRY 241b April 6, 2006 Dr....

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EXAM 3 CHEMISTRY 241b April 6, 2006 Dr. Spurgeon ANSWER KEY __________________________________________________________________________________________ 1. (24 points) Complete the following synthetic reaction scheme by filling-in the necessary starting material, reaction conditions, or product. OH Jone’s reagent SOCl 2 pyridine COCl (CH 2 =CH) 2 CuLi xs. NH 3 NaOEt, EtOH DiBAH CN CHO PCC H 3 O + SOCl 2 O CONH 2 CO 2 H CO 2 Et
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(8 points) Match the following starting material/product pairs with the correct reagent and reaction name. Use a line to simply connect the correct parts. 3. (15 points) Propose a synthesis of the following molecule, using the starting material below and any other organic or inorganic compound. Big hint: the first intermediate you must make from the starting material is a 1,3-diketone. xs. Bromine Then OH - O O O MCPBA Baeyer-Villager O OH O Bromoform O O 1. Base 2. MVK 3. Base 4. H 3 O + , heat Robinson EtO OEt O O OH O 1. Base 2. EtBr 3. H 3 O + , heat Malonic Ester Syn. OEt
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E3,241b,S06 - EXAM 3 CHEMISTRY 241b April 6, 2006 Dr....

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