ProblemSet6 - MAKE ME : 4) Provide the starting material...

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CHEM 3570, FALL 2008 Problem Set 6 Problems for Chapters 4,6 and 7 (7.1-7.11 only on exam – NO MO diagrams!!) 1) Provide starting materials, major organic products or reagents for the following reactions. Remember to clearly show the stereochemistry of starting materials/products where needed. 1) BH 3 2) H 2 O 2 , NaOH H 2 , Pd O NH 2 1) Hg(OAc) 2 2) NaBH 4 OH HO OsO 4
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2) a) Show clearly how all SIX possible products (regardless of if they are major or minor products) of this reaction are formed. b) Circle the most AND least stable carbocation intermediates. HBr 1equivalent of HBr is used in this reaction 3) Propose a SYNTHESIS of the dibromo compound shown using a starting material and reagents containing three carbons or less. (This is the FIRST time you see a question like this. Read the last section of Chapter 6 to get more familiar with this topic. We are asking you to combine chemical steps you know together in a sequence to solve this problem) Br Br TARGET
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Unformatted text preview: MAKE ME : 4) Provide the starting material structure and the reagents needed to transform it into both products shown. You should use two different reactions to complete each task. (This is a similar to question #3 you need to perform more than one chemical operation to solve this problem). O Br O Br Hint : Starting material is a C 7 H 12 diene starting material reagents reagents 5) a) Provide the reagent(s) needed to make the two products shown. b) Draw the most stable conformer of each product. c) Circle the most stable conformer. OH OH OH OH Draw conformers in these boxes 6) Draw clearly the most stable conformations of the following compounds ( A-C ): H H H H A B C NOTE: All these questions are old exam questions from my CHEM359 course. They are hard. Make sure not to get discouraged but instead use them as a guide to assess your skills PRIOR to the exam. The exam will be easier...
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ProblemSet6 - MAKE ME : 4) Provide the starting material...

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