Exam 2 2003 - Name F.03.210E2 Page 1 PNC Professor Finds...

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Name _______________________ Page 1 I. (20 points) PNC Professor Finds That MTBE Additive Threatens Drinking Water in States Where it is Not Routinely Used WESTVILLE - An ongoing survey of gas stations in the Midwest reveals that MTBE, a common gasoline additive, is present in sites where it is not routinely used, posing a growing threat to ground water in these areas, according to Reynaldo Barreto, Ph.D., an associate professor at Purdue University North Central in Westville, Ind., and the study’s lead investigator. The study was described by Barreto on Aug. 30 ,2001, at the 222nd national meeting of the American Chemical Society, the world’s largest scientific society, held in Chicago. http://www.pnc.edu/cd/news/mtbe.html (a) Complete the following reaction, in which MTBE is prepared as a product. You should also provide the curved arrow mechanism for the reaction. CH 3 I + CH 3 C O CH 3 CH 3 CH 3 + Na complete this balanced chemical reaction and provide the curved arrow mechanism IH E progress of reaction (b) Provide an Energy Diagram for the formation of MTBE. Include the level of the starting materials (label as "SM"), the products (label as "P"), and any intermediates (label as "I-1," "I-2," etc), along with the energy curve(s) that relate them to each other. The overall reaction has a D G˚ of -10 kcal/mol, and an activation energy of +25 kcal/mol. 5 kcal/mol MTBE is methyl t -butyl ether, (CH 3 ) 3 COCH 3 , a common (albeit controversial) gasoline additive. (c) Provide a drawing of the anticipated transition state structure for this reaction. Dashed lines should be used to represent partially forming or breaking bonds, and any partial charges should be indicated. You do not need to show the sodium ion. methyl t -butyl ether MTBE (d) How many signals will there be in the H-NMR spectrum of MTBE? (e) What will be the ratio of the size (area) of the H-NMR signals? (f) How many signals will there be in the C-NMR spectrum of MTBE? 4 6 2 2 2 4 CH 3 C O CH 3 CH 3 Na tBuONa = 2 arrows = 2 SM P SM/P @ -10 = 2 one curve = 2 E A @ 25 = 2 2 3:1 (9:3 is ok) 3 CH 3 C O CH 3 CH 3 CH 3 I d d no partial credit F.03.210E2
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Name _______________________ Page 2 II. ( 33 points) Compound A is an amino acid that was prepared during the synthesis of Belactosin A, a substance that shows modest antitumor activity.
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