Midterm 4 Key

Midterm 4 Key - Chemistry C3443 Fall 2007 Midterm #4 75...

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Unformatted text preview: Chemistry C3443 Fall 2007 Midterm #4 75 minutes December 5, 2007 Instructions: (1) For some questions, you have a choice of which problem(s) to answer. For these, cross out (X) answers you do not want counted. (2) Notice that for each question, we have suggested how much time you spend on that question and indicated how many points it is worth. We suggest that you first go through the entire exam and answer the questions that are easier for you and then go back to the questions that are harder for you. (3) Put your name at the top of each page. (4) Unless indicated otherwise, all structures should be skeletal (line) drawings. The exam contains 14 pages (including this face page). The total number of points is 100. I. 1. 2. 3. 4. II. III. IV. TOTAL: f 100 Name: L68 page 2 I. For each of the reactions shown below, fill in the box with the appropriate reagent, major product or starting material. For reagents, number (1), (2), etc. if more than one transformation is required. Also, make sure to include solvent and bases if appropriate. If NO REACTION occurs, write “NR”. Choose 3 of the 4 problems. (15 minutes, 30 points total) (1) Br (2) Mg", Ergo Name: % page 3 I. continued. (3) (4) Name: Liar page 4 I]. For the following reaction, (1) draw a detailed, arrow—pushing mechanism and (2) state the name of this reaction. (7.5 minutes, 15 points total) + I Mb", ( cone _\\C02Me \ MeOZC heat cone Name: K446 page 5 11]. You oxidize cyclopentene to glutaric acid using KMn04. To confirm that the oxidation worked and the oxidation state of the product, you take 'H NMR and IR spectra of your starting material and product. Shown below are the 1H NMR and IR spectra. (1) Draw the molecular structures of cyclopentene and glutaric acid. (2) Indicate which 'H NMR and which IR spectrum corresponds to which molecule, explicitly naming at least 2 key peaks to justify your assignments. (3) Based on the spectra, justify your conclusion as to the oxidation State of the product. (20 minutes, 40 points total) TIINR‘EI‘FTI’IKEI KI 4m 3000 ED“ "mml‘l lilfl 1000 m o 0 CU MP6“ amatan‘c (Lei cl 5”. 1?- shows firm- medm (pm-aim homo. c,=—o Wm od- I‘lOOcm" 4* 0—me add o-H peak , confiwning ended-ton an W woud’ifl Wood. [No o'H sear— mochLbe peso/t bD’afldzhxchQ —9 WW NHE-dpfiiffl‘i’ ‘éYbLQ—Hqg o-H Prom, bud-doeswefi ‘H’U dJSCLPPeDJ'QHCF 04 “HM d-OU-ble bond (loss. 09 CFC—Hi Name: *Qog— III. continued. TlflflfivfllrflfltEl 'U page 6 Name: #— Page 7 [11. continued. 1 1 10 9 8 '? 6 5 4 3 2 1 O HSP- 04-375 ppm a: 0-H meDnS- r‘nafi be bmaGLq- oFFsej- Fag”: ll PPm Name: 132%. page 8 1]]. continued. fiatch £81100) indicad’es C‘sc-“H 1 1 1 O 9 8 7 6 5 4 3 2 1 0 HSP- 03—555 ppm Name: Eva: page 9 IV. Propose a sequence of reactions that will allow you to accomplish the transformation shown below. You may use any compounds containing zero, one, or two carbon atoms. Your answer should be given in standard "synthetic" notation, i.e., starting material, arrow with reagent, first synthetic intermediate, arrow with second reagent, second synthetic intermediate, arrow with third reagent, etc. HINT: Even if you are not sure of the entire answer, work in the forward and reverse directions for partial credit. (12.5 minutes, 25 points total) Bf /"'"‘“----T: r r 0” _a +‘ H( Hozc" war. ‘% \ :9 O D wwws fl :1: Ha H—-C.ECr H ‘fi‘fiflifig L—AHMWS 2" J ‘7” 2e WW3 M004, OH CDZH Er? o a Bozc'flo H5 0 a ...
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Midterm 4 Key - Chemistry C3443 Fall 2007 Midterm #4 75...

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