Sn2Sn1-SA-S10 - The Kinetic Control of Substitution...

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The Kinetic Control of Substitution Reactions Study Problems 1) Which pair will react faster via the S N 2 mechanism. What factor is important in each decision and draw reaction coordinate diagrams that display the rate differences. a) CH 3 CH 2 Br + OH CH 3 CH 2 Cl + OH b) Br + OH Br + H 2 O c) Cl + Cl + OH C O O H 3 C d) I + OCH 3 I + OCH 3 CH 3 OH DMSO
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2) Consider the following reaction. C CH 3 I H 3 C CH 2 CH 3 + H 2 O C CH 3 OH 2 H 3 C CH 2 CH 3 + + I _ a) What is the rate law for this reaction? b) What happens to the reaction rate if- 1- The leaving group is changed to Cl¯ 2- The solvent is changed from water to DMF (dimethyl formamide…look it up!) 3- The sustrate is changed to a 2º substrate 4- The concentration of H 2 O is increased by a factor of 5 5- The concentrations of both the substrate and H 2 O are increased by a factor of 5 3) Rank the following substrates in order of increasing S N 1 reactivity. Explain. a) Br Br Br b) Br Br Br c) Br Br Br CF 3
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4) Determine the predominant mechanism for nucleophilic substitution, draw the product
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This note was uploaded on 03/29/2010 for the course CHEM 152 taught by Professor Grall during the Spring '08 term at University of Arizona- Tucson.

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Sn2Sn1-SA-S10 - The Kinetic Control of Substitution...

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