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prob_05 - Problem Set#6 5.12 Spring 2003 Due Monday March...

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Problem Set # 6 , 5.12 Spring 2003 Due Monday, March 31, 4pm 1. a) Rank the following series of molecules based on reactivity in an S N 2 reaction (NaI/acetone). ( 1= fastest S N 2, 4= slowest S N 2) Me Me Me Me Me Me Me Me Cl Me OTf Me Cl Me Me Br b) Rank the following series of molecules based on reactivity in an S N 1 reaction (EtOH/heat). ( 1= fastest S N 1, 4= slowest S N 1) Me Br Br OMe Br Me Me Me Br Me Me Me Me c) Rank the following series of molecules based on reactivity in an E2 reaction (NaO i Pr/ i PrOH). ( 1= fastest E2, 4= slowest E2) Me t Bu Br Br Me Br Br Me i Pr
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2. a) Predict the product of the following reaction, and provide the mechanism for its formation. Br Me K + – O t Bu Me Me t BuOH b) Draw a picture of the transition state for the above reaction. Pay attention to stereochemistry! c) If the same molecule were heated in diisopropylamine ( i Pr 2 NH), would you expect the same product that you drew in part a ? Why or why not?
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3. Predict the products of the following substitution reactions, and specify whether each proceeds
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