Midterm 3 Key - page 1 Chennstry C3443 Fall 2006 Midterm#3...

Unformatted text preview: page 1 Chennstry C3443 Fall 2006 Midterm #3 75 minutes November 13, 2006 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 he skeletal (line) drawings. _ The exam contains 10 pages (including this face page). The total number of points is 100. P‘P‘PP’P?‘ I}. III. 2 prwr TOTAL: 1100 Name: K 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 sureto include solvent and bases if appropriate. If NO REACTION occurs, write “NR”. Choose 4 of the 6 problems. (20 minutes, 40 points total) (1) CH _ H excess HBr Q“ C?" -— " ‘ -C. 3 E120 B a (2) . / m L,‘ W Nat, (3) CH3_CEC_H _—..NQN“3 CH3—CaCie NaQ NW5 KEY :- Name: Page 3 II I. continued (4) '0 Cl AA k... MeOH M k (5) mCPBA W ——r- CHZCIQ (6) Kéi Name: page 4 II. For the following reaction, (I) draw a detailed, arrow-pushing mechanism and (2) show the major product(s). (10 minutes, 20 points total) Name: L___—_ page 5 _ Ill. Given the following Bond Dissociation Energies, (1) circle the reactions below that are exothermic. (2) Based on your answer to part 1, what would you conclude about the impact of hydroxyl radicals on living systems. (10 minutes, 20 points total) Bond BDE g Ecallmol 1 HO-H 119 CHa-H 105 CHas-H 91 ' CsHs-H 1 11 ’\\~L~\ &%wQ<. 5M— W5 05} m1 Muix nék'ws {Ix ‘M. \(p‘m‘ \ Emu, 59°05 M 63‘wa mx NV) 0‘ banks) (n Ert'p:\.‘w}.x\-y WVN~ Mons, Name: E a page 6 IV. Draw detailed, arrow-pushing mechanisms for the following reactions. Your mechanism should account for the observed stereochemistry. Choose 1 of the 2 problems. (10 minutes, 20 points total) (1) The following reaction gives a mixture of two products. Name: page 7 IV. continued. (2) The Hofmann Rearrangement is an efficient method for converting amides to amines. 3 NH; 13:2, NaOI—I N #- ' m TERI—120 *0 hydrolysis ...
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