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Problem Set VII Key - Name K Q\4 Chem 343 I Spring 2009 TA...

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Unformatted text preview: Name: K Q \4 Chem 343 ' I . ' Spring 2009 TA Name: Problem Set VII Discussion Secition # , . ’ - 1. Consider the reaction of 2-chloro-2—methylpentane with sodium iodide. \/\i/ + NaI --—-> \/\}/ +gNaC1 .' I CI ‘ Assuming no other changes, how would it affect the rate if one simultaneously doubled the concentration of 2-chloro-2-methylpentane and sodium iodide? A. No effect It would double the rate. C. It would triple the rate; D. It would quadruple the rate. E. It would increase the rate five times. 2. What would be the major product of the following reaction? E. Similar amounts of I and III 3. Which is the most reactive nucleophile in DMF (structure shown below) ? OF B. Cl" C. Br" D. I' E. They are all equally reactive. 4. Which substitution reaction would take place most rapidly? A) ' H20 ' , _ OH +‘ CH3C1. W CH3OH + Cl B) o i . o . H20 . _ + CH3Cl ————;——> + Cl Hat) 0' - _ 25 C H3CO CH3 C) H20 + _ H20 + - CH3C1 W CHSOHZ + Cl , D) CH OH T + H l *9 0+ + ' CH3OH ‘C 3C 250C H3C/ \CH3 Cl @ - " - ‘ SH + CH3C1 ——-——> CH3SH + C1 0 5. The Hammond-Leffler postulate when applied to nucleophilic substitutions and elimination ' reactions states that: A) a negatively-charged nucleophile is stronger than its conjugate acid. B) polar aprotic solvents strongly accelerate the rate of 5N2 processes. C) bimolecular nucleophilic substitutions are 211d order kinetically. .the transition state for an endergonic reaction step (one accompanied by an increase in free energy) resembles the product of that step. E) elimination reactions will always compete with nucleophilic substitution reactions. 6. Which alkyl halide would be most reactive in an SNl reaction? ‘ 7. The major product(s) of the following reaction would be: ' 4 CHZCI OH" ‘ §' -—-—————->- H CH3 E. Equal amounts of I and II 8. Which 5N2 reaction will occur most rapidly in a mixture of water and ethanol? @ r + CHgCHz—Br ——> CH3CH2—| + Br' B. l' + CH3CH2-Cl ——) CH3CH2—l + Cl' C. r + CH3CH2—F ———'——> CHgCHz—l + F" D. Br" + CHgCHz-Cl ——-——-—————> CH3CH2—Br + Cl" E. Br‘ + CH3CH2—F ——-——-—‘-——-) CH3CH2—Br + F- 9. Which alkyl halide would you expect to react most slowly in an SN1 reaction? @ (CHalac’F G. (CH3)3C-C| H. (CH3)3C-Br * I. (CH3)3C-I J. They will all react at the same rate. 10. The mechanism of the following substitution reaction and the product(s) formed would be: .sNz,’ I only B. SN2, similar amounts of I and II. C. SN1, I only D. SN1? similar amounts of I and II. 11. The mechanism of the following substitution reaction and the product(s) formed would be: . 8N2: I only . 8N2, similar amounts of I and II. G.,SN1 I only @ SN1, similar amounts of I and II. 12. Draw a stepwise mechanism for the reaction shown below. Use curved arrows to show the movement of electron pairs in each step, and draw structures for all intermediates formed on the - way to the products. Be sure that your mechanism accounts for the stereochemistry shown for the products. ' racemic ...
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