04 - Problems

04 - Problems - have learned this semester. In each case,...

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Chem 112A, Fall 2010 - Problem Set 4 Due by 5pm on Friday Nov. 5th, 2010. You are encouraged to work in small groups for this assignment. Write your name AND your lab section on the problem set before submitting it. 1. Provide the major product or products that would be obtained for each of the following reactions. Also label each one as S N 2 , S N 1 , E 2 , or E 1 over the arrow. In some cases more then one of these reactions might occur. If you would predict that no reaction will take place (or it would be terribly slow), write ‘No Reaction’. a. b. c. d. e. f. g. h. Br S O - + DMF I + DMSO O - I + DMSO NaCN HOAc CH 3 I + DMF N - Br + DMF CH 3 S - Br I O O - + HOAc + DMF NaOH Cl
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i. j. k. l. 2. Provide a suitable alkyl halide and a set of reaction conditions that could be used to obtain each of the fol- lowing alkenes as the major elimination product. There may be more than one answer in some cases. a. b. c. d. e. + THF N - Br + HOAc Br NaOAc OH + DMF I - MeOH/K 2 CO 3 Cl O O
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3. Each of the following overall transformations can be achieved by combining several of the reactions you
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Unformatted text preview: have learned this semester. In each case, provide a clear reaction scheme that shows how to convert the starting material into the fnal product. Be sure to show the structures oF all intermediate compounds. a. b. c. d. multiple steps O Cl O OH (racemic mixture) multiple steps OH HO Br OH multiple steps Br CN multiple steps HO 4. Use a reaction coordinate diagram to compare the energetics of the following S N 2 reaction in (a) a polar aprotic solvent, and (b) an apolar solvent. For the purposes of this question, assume that the starting mate-rial, product, and NaI are equally soluble both solvents. 5. Use a reaction coordinate diagram to compare the energetics of the following S N 1 reaction in (a) a polar protic solvent, and (b) an apolar solvent. For the purposes of this question, assume that the starting material, product, and NaI are equally soluble in both solvents. + NaI Br I different solvents Br + NaI different solvents I...
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04 - Problems - have learned this semester. In each case,...

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