Measured by following the incorporation of

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, measured by following the incorporation of radioactivity into the iodooctane. Under identical reaction conditions, the second order rate constant for the change of the optical activity of the solution starting with pure ( R )-2-iodooctane was measured to be nearly double that of k s . a. Is this data consistent with inversion of the stereochemistry in the SN2 reaction mechanism? Briefly explain. c. How is the data inconsistent with an SN1 type mechanism? b. Remember no reaction mechanism is ever proven, only mechanisms that are inconsistent with experimental observations can be excluded. How is the data inconsistent with a front side attack reaction mechanism. a. Estimate the conjugate acids pKa and then rank the following anions in order of leaving group ability (1 best, 6 worst). Br - CH 3 CO 2 - CF 3 CO 2 - CF 3 SO 3 - CH 3 SO 3 - H 2 O c. Sodium acetate is a better nucleophile in an SN2 reaction in dimethylformamide than in formamide. Briefly explain. 3. SN2 concepts and curiosities. estimated pKa of the conjugate acid rank O N H H H O N H CH 3 CH 3 b. The following rate data for the reactions of CH 3 I with three different nucleophiles is provided in two different solvents. Comment on the significance of these results regarding relative reactivity of nucleophiles under different conditions. nucleophile Cl - Br - NCSe - k rel , CH 3 OH 1 20 4000 k rel , DMF 1.2 x 10 6 6 x 10 5 6 x 10 5 Chem 33, Kanan & Stack, 2012, PS 7; pg 2
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4. Intramolecular cyclization reactions. a. Cyclization reactions that proceeds through an SN2 mechanism that are intramoleculear are generally always faster than intermolecular exaples. Using the rate law for such reaction, explain why (N = nucleophile; L = leaving group).
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