PS6_Solutions - CHEM 3570, FALL 2008 Problem Set 6 Problems...

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Unformatted text preview: CHEM 3570, FALL 2008 Problem Set 6 Problems for Chapters 4,6 and 7 {7.1-7.1} only an exam — N0 M0 diagrams! I) 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 @v ‘_H—’2 H202, NaOH 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. iequivalent 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. Cl" his is the FIRST time you see a question like this. Read the last section of Chapter 5 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) 3. ~ TARGET )figr/v MAKE ME : H[ gr /l\f;r =7 /¢“q : ////\/ _ ,ZH («r—— _¢_w_ 9 / i BC: j H: / a + Lind!" A’s-“Ht 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. (T his is a similar to question #3 — you need to perform more than one chemical operation to solve this problem. . .). Hint: Starting material is a C7H12 diene . . rea ents starting material 9 I) 8143 2) MaOl-l, [4101 3) 3.1 I )—<—Br >EO>—\Br 0 5) 3) Provide the reagent(s) needed to make the two products shown. b) Draw the most stable conformer of each product. 0) Circle the most stable conformer. _ it the/t z) Maori , H10 LAC atlu-Hy “I”; L 4m; lies 0... 6) Draw clearly the most stable conformations of the following compounds (A—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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This note was uploaded on 10/26/2008 for the course CHEM 3570 taught by Professor Ganem, b during the Spring '06 term at Cornell University (Engineering School).

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PS6_Solutions - CHEM 3570, FALL 2008 Problem Set 6 Problems...

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