Problem_Set__6 - Problem Set#6 Swager 5.12 Due Friday Oct...

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1 Problem Set #6 Swager 5.12 Due Friday Oct. 21, 2011, 4:00PM 1. Rank (1=most stable) the following radicals in order of their stability.
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2 2. Consider the reaction of propane with hydrogen peroxide shown. Suggest a detailed mechanism. Which product would you expect to be formed in the largest amount. Explain your reasoning using a reaction coordinate diagram. + OH OH + H 2 O HO-OH, ! or h "
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3 3. Suggest the best reagents and show all intermediates for the following transformations. HO H 3 CH 2 C H 3 C OH CH 3 HO H 3 CH 2 C H 3 C OH CH 3 + Enantiomer + Enantiomer
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4 4. Give the products of the following reactions. Show all stereoisomers. + Br 2 /H 2 O (Z)-3-methyl-3-hexene 1. BH 3 2. H 2 O 2 /HO - HBr and Heat and small amount of R-O-O-R 1. O 3 2. S(CH 3 ) 2 1. catalytic CF 3 SO 3 H 2. H 2 O quench RCO 3 H
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5 5. Suggest the reagents to best carry out the following transformations. More than one step may be necessary and you should draw upon all of what you have learned in 5.12.
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