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UT Knoxville CHEM 360 - exam 3 answer key spring 2013

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~ 1\/11'\.,c.Chern 360 Exam 3 Spring 2013 NAME~)ljl--_l)(J __ '~ _Prof. Bartmess (Carey 8)CS- This is a 55 min exam. Please think your answers1. (13) through before committing them to paper.- Be legible; in can't read it, it's wrong.2. (08) - Don't put any answers on the back of the pages(although you can use the backs for scratch paper);3. (43) material on the back of pages will not be graded.- BE SURE YOU HAVE FOUR DIFFERENT PAGES4. (15) -put your name on the back of the last page by the staple5.(21)1.(13) Give the correct IUPAC nomenclature for the following structures (ignore RlS).(j)QNH2 ~yyOEt1»<:,CH~NH 0o~ ':!~~-+1+(?-ClNV\.~V\Dbu.-rtlV\Oa.:tt-·t-tS-D...W\( -o -f -gXI)-..rl+'n~OJv\tJ---:0+1t>r-cl.v...t-l'tfst-t-/-(t9V'~+-1.:tf.:St-\+1-t-(2.(08) For each of the following horizontal groups of 3 acids, indicate which is the strongest acidon each line by writing "strongest" under it, and which is the weakest by writing "weakest"under it.~vy;n~OEtoIIc/ '-.....OEtH3~·t-2eeL-o0AAooPhNH3+NH3+02Ns-tn7V\~H20~3.(43) Fill in the missing reagentlreactant/product(s). Show all organic products. Pay attention toregiochemistry and stereochemistry. One arrow does not necessarily mean only one step or set ofreagents.PhNH21" 2.. -'- (~)NaVV'l-J(-fC{!~ a....PhCN~b.,) C-lLL0.~:s••yt-yfW\ ~~+l..(}Au.\.cV'+.Label major, minor~J\J~xs MeI••Ag20-----Ll/'~ c./.) d.1) LiAIH4' Et20PhCN2) H20Me2C=OtBuNH2••NaBH3CN~/-d34/ . '\ I-f+-s~,.•..t.\JV\-("'-'l+-L.-'Phct{2- tJ1{'L -l-'S-:Se.2. H30+MIA\~j=X -v,LPam~·Addu-.-+2-~1. nBuMgBr, Et20••Sf.-1'::2 ,C?+t-+-1'J~1-'-z)MO~Uz.-C)n~ tft..~2..-~-I 1.. ~NH2d:. ~I)N3-8-3)'i) ~M.JI~0'+-otr\OI2]+dJ~{~}-c~k='O"HO-< l-N=N-( l-CH=Organicpieces) "f-~6~u..'CLjt-L~~Br~h.PhC02Et+o~EtO-H30+••••EtOH.+~?h vCD'l-H1&\#tCf)~/-/&!tM~I~2DcP-lftP<-P'"<;«'~V'_T8-}~l-hL-(Lct(~\~I ,1/'t '~sy~~~ p~~-isMcl5tfl-\eQ ~tj\NCQt~,p:~3t'~CP4Lo~aL2-- ~/-CM234.(15) Present a high-yield synthesis of one the following molecules, starting from whatever ofthe following are needed: non-cyclic mono-functional alcohols of four or fewer carbons,benzene, C02, and/or cyanide, plus any necessary inorganic reagents. You need not give themechanism for each step, but all necessary reagents and solvents must be shown, and eachchemical step (different reagents) must be clearly indicated as a separate step.Fo~Ph11+6Iki5F'f/~.\~1-0'\---r ,-'eJ)~It\JQ~l.-- -{2-kc.Q+l~ f'\.ll-{L--D'Y['1-~~1\\C?~ef'-'fef2-\;t"cQ..l- (~\ 0....,-'1Ut~~JIJ.;j;;O'f4-L.no)_/Atr>!CfL2-XJ2Q3-I'v@"C£VI\\ot.wt,~t)Sod."2.. {'Yl..\f"~\z)e;--t'OM ,c:""lv61{,~t*A-+J5. (21) a. Give a complete curved-arrow mechanism for the following reaction. Show allintermediates and any important resonance forms for them.r-7l"L-\~c)~o-to(f1~ ~ .•, 1 eqv. Br2~ PhCH3n3u ,n2u•J _t.C>-~-\'\l ~&--7?\n/"cM~ci91Hte~2?~~~2 {Hbl-fl@l:>~<r -~'"-+16H, +c'Ph" "'Cll3>@+<oII-rPh~Br+~~+LOs-tV'-u-J-·+HBr~dfLtJL~-4lC5f1.f0.....-1-1(42.)l7(" ......---\. ~~vCxh_6V'?h -@ ~+fy- ~b. If this reaction is run as shown, but with excess Br2, are other organic products obtained inJaddition to the above one? Why or why not?~ ~ V\,()'Bt-?3\{'tfW\l)~ ~~


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