Midterm 4 - Name: page 1 Chemistry C3443 Fall 2007 Midterm...

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Unformatted text preview: Name: page 1 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: / 100 Name: 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 (I), (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 0 (2) Mgo, Eth IVanue: I. (3) (4) confinued. mg 0 + If —._>. heat NaOtBu tBuOH page 3 Name: page 4 II. 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) / COZMe .‘\C02Me + l —+ \ MeOZC heat cone Name: page 5 III. You oxidize cyclopentene to glutaric acid using KMnO4. To confirm that the oxidation worked and the oxidation state of the product, you take 1H 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 1H 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. (15 minutes, 30 points total) [DD 53 TRIHSI‘H TFRNL'EI 2| IMO 3900 2005 film 1.000 film IIFl'I'EHUflI {RI -u| Name: page 6 III. continued. [00 IT IIHSHIITTIMCEI kl an c: “100 3000 goon 1500 1000 EEO HFWENUHI ERI -1| Name: Page 7 III. continued. 11 10 9 8 T" 6 5 4 3 Z 1 O HSP—D4—8?5 ppm Name: page 8 III. continued. 1 1 10 9 8 '2? 6 5 4 3 2 HSP-DS-SES ppm Name: 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) HO C a Br ——I-— 2 WCOzH —I- O Name: page 13 Table 12.1__§ Characteristic IR Ahsprptions of Someflmctinnal Groups M r0m_..___m_m._._._..__ _ "Tumm_mmm_u_,.0mmwku,.0-0,,.__...__m.._..._...n_«__.._fl_.-._.w_m._. Functionalfiruup . AhsorptioMcm") Intensity ' if Funclionaleup Absorptionicm“) Intensity :-'Alkane I Amine C—H 2850—2960 Medium N — H 3300~3500 Medium Alkene _ t C—N 103(L1230 Medium :c—H 3020—3100 Medium Carbqnyl compound c=c 1640—1680 Medium 0:0 1670—1780 Strong Alkyne Carboxylic acid EC—H 3300 Strong 0—H 2500—3100 Strong, mead- CEC 210042260 Medium I Nitrile Alkyl halide _ ' ' (3-20! 2210—2260 Medium C—Cl 60€PSOO Strong ' Nitro : C~Br SOO#6OO Sm)th ' N02 1540 Strong EAicohol ' ' I I 0—H 340073650 Strong, br0ad ' c—o 10504150 Stftmg - I ene I C—H 3030 Weak- momma ring 1660—2000 Weak-_ 1450—1600 Medium E I i - E E E i. ! page 14 Name .____w.u.,M_,‘._: EzmlgmhfiE'Mfifimygmwmmm_.-..__ 5 S x Tabie 13.2 Chemical shift (5) ...
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This test prep was uploaded on 04/07/2008 for the course CHEM C3443 taught by Professor Cornish during the Fall '08 term at Columbia.

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Midterm 4 - Name: page 1 Chemistry C3443 Fall 2007 Midterm...

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