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

Problem Set 8-Solutions
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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): 7) 3-Carene (the compound shown) is a component of the oil of turpentine from the tropical 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 the reagents provided except in the m-CPBA case). excess m-CPB // lHQ{OACh H20 0 E 0H 5" 9) Menthol, the major component of peppermint oil, is widely used for flavoring and as fragrance in confectionery and perfumery. We discussed it in class when we were learning about (R) and (S) assignments. When the compound shown is hydroborated and oxidized (reagents shown) natural menthol is obtained. Given this information, draw the structure of menthol in the box provided and draw the most stable chair fdrrfi of it in the box below. 6 EtzBH then H202 ——-——)-— = OH A I Menthol Chair Conformation of Menthol' 10) Provide the starting material and a detailed reaction MECHANISM. _ Br2, MeOH \/ :0— Br FC‘Br 3’) H6Me Br ‘H Br _ 0— {fi_ —. Hu‘“ O : \ — Br 5 H Me J Enantiomers B: W— Br 11) Provide starting materials or major organic products for the following reactions. Remember to clearly show the stereochemistry (relative and absolute) of starting materials/products where needed. 0 —-'—"‘—'E Hg(OAc)2 H20 —--——h- excess 0 EXCESS HBr , IIHIIII- H2, Lindlar catalyst ...
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