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Problem Set 8-Solutions - CHEM 3570, FALL 2008Problem Set...

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Problem Set 8-Solutions

Problem Set 8-Solutions - CHEM 3570, FALL 2008Problem Set...

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Unformatted text preview: CHEM 3570, FALL 2008Problem Set 6Problems 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 followingreactions. Remember to Clearly Show the stereochemistry of startingmaterials/products where needed.1) BH@v _H2 H202, NaOH 2) a) Show clearly how all SIX possible products (regardless of if they are major orminor products) of this reaction are formed. b) Circle the most AND least stablecarbocation intermediates.iequivalent of HBris used in this reaction 3) Propose a SYNTHESIS of the dibromo compound shown using a starting materialand reagents containing three carbons or less. Cl" his is the FIRST time you see aquestion like this. Read the last section of Chapter 5 to get more familiar withthis topic. We are asking you to combine chemical steps you know together in asequence to solve this problem)3. ~ TARGET)gr/v MAKE ME :H[gr/l\f;r =7 /q : ////\/ _ ,ZH(r __w_ 9 /i BC: j H: / a +Lind!" As-Ht 4) Provide the starting material structure and the reagents needed to transform it intoboth products shown. You should use two different reactions to complete eachtask. (T his is a similar to question #3 you need to perform more than onechemical operation to solve this problem. . .).Hint: Starting material isa C7H12 diene . . rea entsstarting material 9I) 81432) MaOl-l, [41013) 3.1I )<Br>EO>\Br 0 5) 3) Provide the reagent(s) needed to make the two products shown. b) Draw themost stable conformer of each product. 0) Circle the most stable conformer._it the/tz) Maori , H10LAC atlu-Hy I; L4m; lies 0... 6] Draw clearly the most stable conformations of the following compounds (AC): 7) 3-Carene (the compound shown) is a component of the oil of turpentine from thetropical pine Pinus longifblia. Show the major product one would obtain by treating 3-carene with the reagents shown (stereochemistry).HCI 8) Draw the major product of these reactions in the boxes (Use one equivalent of thereagents provided except in the m-CPBA case). excessm-CPB// lHQ{OACh H200 E0H 5" 9) Menthol, the major component of peppermint oil, is widely used for avoring and asfragrance in confectionery and perfumery. We discussed it in class when we werelearning about (R) and (S) assignments. When the compound shown is hydroborated andoxidized (reagents shown) natural menthol is obtained. Given this information, draw thestructure of menthol in the box provided and draw the most stable chair fdrr of it in thebox below.6 EtzBH then H202-)-= OHAI MentholChair Conformation of Menthol' 10) Provide the starting material and a detailed reaction MECHANISM. _ Br2, MeOH \/ :0Br FCBr 3) H6Me Br H Br _ 0{_ . Hu O : \ Br 5H MeJ EnantiomersB: WBr 11) Provide starting materials or major organic products for the following reactions.Remember to clearly show the stereochemistry (relative and absolute) of startingmaterials/products where needed.0-'"'E Hg(OAc)2 H20--h-excess0EXCESSHBr ,IIHIIII- H2,Lindlar catalyst...
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