Chern 360 Exam 1 25 Sep 2013 NameProf. Bartmess (Carey 8)u ~ ~j)Q31. {12}2.{06}3.{4S}4.{21}5. {16}- This is a 70 min exam. Please think your answersthrough before committing them to paper.- Be legible; if! can't read it, it's wrong.- Don't put any answers on the back of the pages(although you can use the backs for scratch paper);material on the back of pages will not be graded.- In addition to putting your name in the above blank, also puton the back of the last page (only) of the exam, by the staple.Be sure you have 4 pages1.(12) Give the correct IUP AC nomenclature for the following structures (you can ignoreR,S) (J)iHc!JOEtOMeICICH2CH2CH2CHCHCH(CH3hIOHCI"7-~lo!:p -if ~~~+-1+i-2-~"'3-£~- ~-~f'( ~ (-t-1·:tFS+-(() r-d.v-.-+-,s-cOAtoro -.-~~.-2--e.-~ -E~J.-,-----of'-t-I~5 ~\O~-rt2.(06) Circle the side of the following acid-base equilibria that is favored (higherconcentration) at equilibrium.30LnBuLi+Nlb •• ~+~MeOH + iP~ MeO-Na+ +iPrSH~~ g.~ C)?/r~><"J -,00r(U "-u'l:MeK~~'x..00--&-...,..,.flo -: ~. (45) Fill in the missing reagents/reactants/product(s). Pay attention to regiochemistry ~:nd stereochemistry. One arrow may represent multiple steps; show them all clearly.~.!(-'3crCH=OHN03 ~ CUOI •.,.-9I ,-'LW ~~ H2S04--r;D7--/zJl{j\D0-S03_~stfC'+-~I+2)\ jCI •0?-~~~lCpH2S04(~702N~l 'Lb,IJ) ~ero()1:fu~e\rCtY-t~ OH - o-t'kuL - '-:~-U--\-t-~-~-+-::----=~~t""·l)""-tBuc'f1t -'? /' \r-f11MJJ-3,,0ckkcktJL~~e.~O/tBU HI..tBu.Tcfl/-l-~6.Z'~uJ6-t;i - ~@\;t~ OHfi=-Q1JWW~ .•L.(,;1.'--b.c.d.o~OH1) LiAIH4' Et20••~~2)H30+f.oH2S04-2-W~o4( .-7-W~•MeOHh.CuI PhInPrLiph~Y\r'vc.\;'\ -::C\i\.t.-."",\......1...fl~i!)H~~JM&~ .••.101CH,CH,CH,'B:I~~-V~/H-Th:\-'bhJJPVL. ~W .~ ~ rJ-tlf+l ~+~+(ofto4.(21) Draw a complete curved-arrow mechanism for the following 'reaction, showing allintermediates and their resonance structures.•N02OCIo..J\..::--'<Ur1.-Uh..{Lb'-LN\~~~-;-]2-4@,+-'?6C12FeCI3.•.o.JUL1vv..,LU-A-- .OVV\~ .u.~~~\a.:t.,U,:;l-fk@tsv:"JiJ2-@)+-• -r ~CSL-~&3<V,"3'~L .+0@Bl~ ''LffbtJU ''l-CQ ~'2-- " '.CQ ,~~ ,,~L~-t<, .i-f~~~'::::::::::-- [i. ~....--- ~. -~ ., .~ .,-r~J:- ~ ~ ~ \~~ -:CQ.~(Q3(B)1-+31l+/~ . ~~rp1-,CQ1C:;(cQ -cJ1'..~e.cSL'3d-+~b. Circle the straight reaction arrow of the slow step in this reaction.c. Will this chlorination be faster for the nitrobenzene shown, or for phenol?Draw the one intermediate resonance form that makes the faster one faster:+\f>k~+z> \-{~\}~+\~"~ceun·:;tiL~nfin!~·D38[;J~rJ.U..ti:O{r~.n 'Bnn1f; ,.'--....".....~..•.#••••••••.•••••••••>~ ,...•••...; ..#.,.•••••.•••••••••, ·, ••••..v.,·_'"'""_ ..•.".,...•.•..•,v.",,-,~.,·,.-;~~....•.~.•..•.~.•...•._._"''''"_~''.'.~.••..•~.~__., __.,,,..F>;. So·t' ;.4 .."/'t1~'"'·~-.·~,.-···~~"""......•~ ~-,'.'0~ 5.(16) Here is the proton nmr spectrum of a molecule C4HgCh. The delta units are the{... ~0tf0mmost numeric line.&9ive:. the correct structure of the molecule, CIRCLING IT SO IT CAN BE TOLD FROMOUR WORK..+\ -Label the hydrogens in your structure with the pertinent "A", liB",etc. labels shown on the~ _ eJ.Y.-spectrum ..C,*.J -~. .-Bl31~fLY, show your reasoning; mention chemical shift and splitting or the lack of it for each~ '-t ;leak.Extra Credit(5): ~~1at is the structure and name oftl~\.chemical that gives the marker signal at 0=O.O?l~,\ ~.~"" ~~~ ""~@('iJ'1-)--- OLlCkAb'=cJ-t.~D'3~1f\JL>l-T'~tH·C-B.A-A~..lnn'HlHfi"<.~A:IH B:2HC:2H D:3HcJv{L - ~c:LQc.B.~~~~..,.~~.~.-~,= ~.- ~-~3(J..(L-ct(2---c.l-{&..- -cA-t ----'\"Z-!{U\.LJt--e-tb3~·2.-H: t~ 10 l-H==--~2-c.J-h.:--lt{U\.JL¥.-+-t.c:J(Iv"'O-Av~ulv6 .-d4'L-.-\ V\8---V\~-tin&l3dBthL\r(L ~.I~cQ:--ct-\1-.lYl--Acu-yL•.