Microsoft Word - SN and E mechanism problems spring 2008

Microsoft Word - SN and E mechanism problems spring 2008 -...

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1. Answer the questions below for the following S N 2 reaction: (a) Write a complete mechanism including the transition state for this reaction which clearly explains the stereochemistry of the product. H 3 C CH 2 CH 3 Br H CH 2 CH 3 CH 3 H I + + NaI NaBr acetone (b) What is the rate expression for this reaction? (c) Fill in the relative rates of alkene formation under the conditions given below [RBr] [NaI] relative rate 1.0 1.0 1.0 2.5 1.0 1.0 0.5 2.0 3.0 (d) How will the rate and/or the products change if: i. The substrate was 1-bromobutane instead of 2-bromobutane? ii. The substrate was 2-chlorobutane instead of 2-bromobutane? iii. The nucleophile was NaF rather than NaI? iv. The solvent was hexane or methanol rather than acetone? v. The concentration of NaI was cut in half? vi. The concentration of the substrate was doubled? vii. The solvent is 20% water, 80% acetone? (e)
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Microsoft Word - SN and E mechanism problems spring 2008 -...

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