PS_6_Key - Problem Set #6 Swager 5.12 Due Friday Oct. 21,...

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Unformatted text preview: 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. Q (L a?" , g I VLA/ A/W W” 90 O ' "‘ ° (0 Sea “DAEC'” VJ/x‘ 1° N / ' \ 2. Consider the reaction of propane with hydrogen peroxide shown. Suggest a detailed mechanism. Sketch out a reaction coordinate diagram. Which product would you expect to be the dominate one. Explain your reasoning. HO—OH,Aor hv 0” W A A + //\/ + H20 H—o—ou _._=7 Q'O It 3. Suggest the best reagents and show all intermediates for the following transformations. HO OH I _"—" VFW + Enantiomer H30 ’9, chHQC CH3 1H ’57” ‘ a“ i/ g 3 > OX féu HO OH | —p w“ + Enantiomer H C HGEHzc CH3 ‘1’ 0.5 j ,ngs/ W V a v6 4. Give the products of the following reactions. Show all stereoisomers. EN” a: a“ Lfa'n 0“ \fi"' + Brzf‘Hzo —* 4" 9 0H- QHS 9H (Z)-3-methyl-3-hexene _ ,. lie at n +- H-h" 4' —>_. 1.BI~I3 , ""\._. 2. 1120er0 ‘ 15c (3:- r a HB and Heat :\ and small amount of R-O-O-R 2. H20 quench ——-I- . @H 1. catalytic CF3SO3H W" H $4; + .4 1/75» 2. 5((3113)2 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. 6«*a/Mao OH OH I H 3C @OH HO @CHB + 'e C" 50‘? 1'4 * H Q'CE’JVM; Q "sag/[#024 (#03 read: me! ‘50) OEt Br + main Br 6. The following two reactions give the different results as indicated. Draw the products of the reactions and suggest the origin of the differences in the stereoselec:ti vity. Hint— Steric effects. CH3 ——r- One product 1. BH3 Et H202, HO' H3C CH3 CH3 CH3 ———-—I- Mixture of Dlastereomers ,9 1 BH3 *Et 2 H202, HO H C CH 3 CH3 3 blocks- “Ht? Tole. awn-£- “ 4J4»? {Lu ,c .3 1-13 1*: >I\/ / fl —_=) u u /'H 11"”? afluks... ‘4 a b 3" n Pf m 0 ' id - 5‘ o’H Isu‘flfim 0"" T6? “hm (fie/H.102 \‘r -—7 firm ' u 7. Provide a detailed stepwise mechanism using curved arrows to account for the following transformation What is the stereochemistry of the product (which is formed as a racemic mixture)? Br Bl'2 O -—-—I- CHZCIZ 0H non-nucleophilic lvent (I; SO ‘ r—-- 56 4 8. Rank order the following groups of molecules as indicated (1 = highest or fastest) Relative reactivity with e] ectrOphiles Basicity of the carbonyl oxygen 0 O 0 -~ f it?A It “a 5° C + 4—2» L...) g.) CIT .._, +3 " v t % 1w! Relative reactivity with nucleophiles 3 '“W‘M‘e cf: ‘14 9. (Challenge Question- Will not be graded) Using the molecules in the box and any reagents we have discussed thus far in 5.12, propose a synthesis for each of the compounds given. Note that there may be more than one method to produce the compounds. 0H 0 N Br OH HO Produce as a single stereoisomer ‘7 £9 69 l “'_"" + are... “'9 3 we?“ we r s \ 4- °9 N 3 G“ ‘i 31 4 a1 \"'—" "x :_ Ha? ‘ \s :3 fl” L'AJM‘ /:\ l 630 3 coal-d 1' “ m a“ mm mm IgH/fw #02 awe. ...
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PS_6_Key - Problem Set #6 Swager 5.12 Due Friday Oct. 21,...

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