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Practice Prelim #2

Practice Prelim #2 - NAME CHEMISTRY 1570 Summer 2009...

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NAME ___________________________________________ CHEMISTRY 1570 Summer 2009 Wednesday, July 15, 2009 11:00 a.m. – 12:30 p.m. PRELIMINARY EXAM #2 Please do not open this exam booklet until you are told to do so. You will have 90 minutes to complete the exam. Page # 1. _______________ (20 points) 2. _______________ (15 points) 3. ______________ (15 points) 4. ______________ (15 points) 5. ______________ (15 points) 6. ______________ (10 points) 7. ______________ (10 points) TOTAL ______________ Excluding this cover page there are 7 pages in this exam.
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1. (10 points) The reaction of (S)-2-bromobutane with sodium hydroxide follows a second order rate law (the rate is dependant upon the concentration of two reactants) and gives 2-butanol as the major product. Show a mechanism consistent with this rate law using the curved arrow formalism. Show the transition state(s) and/or intermediate in brackets and draw the relevant stereochemistry of the product(s) showing the R or S designation. 2. (10 points) The S N 2 reaction in a Williamson ether synthesis can occur intra-molecularly, meaning within the same molecule. What product would you expect from treatment of 5-bromo-1-pentanol with base?
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