FinalKey_Wi04 - NU Chem 210—2, Winter 20“ Final exam 2...

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Unformatted text preview: NU Chem 210—2, Winter 20“ Final exam 2 1. (20 pts) Complete the following reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. Assume that Friedel-Crafts alkylation can be stopped at single alkylation. “11% a) lxcL b) d) HO 0 Z WW6 (4‘ HO @CN 2) “501.; “W 2’3 OH ( CI 9th v.6,ka (:1 (f9 W 4) Hgo J '{LO WU}? \C:“9 2 /)\070 A», 0 / _ 7 w / 0%“Ufl‘7 ‘ a M 01 _ 'J/K —-— —————-———-—> HzN/V U / Ct A ;) MUM m MAM AC) Mg ,2» — p l 7 c [Hum/qu wa/5 or) ML M OK ")OMIMOL : Z) 050.. Z cutmmm—T TsHN\_/NHTs g 2ch ~— (Equal) 9 LArH 240%) JW 7 fume mfg”, [a . OH 0 1"“ .2 Mug”) 610” O VKQWJJWMJJW m a) CHLIL )5 m O c) o 1)LAH dam [L 2) H30+, H20 ,JLH ‘ f H O 3)M M B ' l (N 02/ ‘ iw e 9 r , ' z / O 4) Hsofi H20 W) W)‘ L/bo ‘\/ (LC M‘wj‘*N 1 .L at a WW [L ,RW/on / // 1' > r (g . f “ t o x K r / - 7K2]; .4 9 c O ) 0U / wa/L’C’“ M +50 NU Chem 210—2, Winter 20% F inal exam 2 1. (20 pts) Complete the following reactions, be careful to give all the major carbon—containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. Assume that Friedel-Crafts alkylation can be stopped at single alkylation. HO HO @CN OH ——————————> Cl C: a) b) 2 path“ 0 HULMM m w _ 2, OgOAt (tho; 1' TsHN NHTs / = “J / C) / ‘ (’Lc, / _ . L UH" " ,_ [IVE I: NOT QCuemvC 4>ZT€WLTS JRUHJ A) .99 rm 6) Lil/[4 New) OH 9) («l-50* UIL ()9 who” i) 0 MM <8 M d) “so? TS‘m O OH e) H' \ ?, 4 93/ M {l} e J~o\;Q/H { 0’ 9th /' f j \(l L NU Chem 210-2, Winter 2004 F ina/ exam 3 2. (20 pts) For a-c, gives the IUPAC name of the structures shown. For d-e, complete the given reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. Cl R — was Sta/aw OH (fl/2, g): “a, , 24,- flung/d; (AC/Col a 8) OH L; b) O a C) {:7 \. d, (T / g” Jag]- mat/new OfL Zv Gaugzma (-47% rZwL ti“ Wr—WWW USL «S MQC We) l * WWW? Wilt 3‘37 0“ my“ K” /L. r” @Il?’ / ?L O “'59)“ Br Br m ONgSJéJ LC“ saw” eff/2; Z 0% a row (5/ 3 PCL 0 5 a C) Q J A \ 3) N 55: d Cf /§._jr 4) W‘sp: B<df\ ,6) a0 AJA t e g) 6ng Lot,“ ,3 g) wet, Z0 at A 3 ’ ’ . /(4L 4,) m ,1; fix Eto 0M 0 m) A,“ at 01L AMA w, b) 2 We QZ‘COlMD 3 lb; / gm‘a A , > 0K l) H ‘30 3) ) A fill/W) 4> aw WSW new '3) Em” QUCO evil ‘3) Mom) A 9) “Eat . f H02 MU} _ b) LHGL JD] )(ACQ (/QZ) [Te/CZ; NR” flzléo’tvkjl at) :t Z L; 1) PM: 8) Nl'éS/W g) FU’ <6) j—w 31.) Kayne“ 4) Ft? NU Chem 210—2, Winter 2004 Final exam 2. (20 pts) For a-c, gives the IUPAC name of the structures shown. For d-e, complete the given reactions, be careful to give all the major carbon-containing products, starting materials, or reagents. Clearly indicate the stereochemistry when relevant. If there is no reaction, say so. Cl OH ©/\N/ b) Br Br EtO , IL _ Q O‘L \(0 a 0 a) 123% W M “ML; , I I ) V)” 1.1,) N85 J64; 352 LLOW“) A g) {c 0%,, ,3 NU Chem 210-2, Winter 2004 F inal exam 4 3. (20 pts) Propose a curved arrow mechanism for the following reaction. Show all the proton transfer steps. 0 HNJ< Q/VO + 2 EtOH NU Chem 210-2, Winter 2004 Final exam 5 4. (20 pts) Propose a curved arrow mechanism for the following reaction. Show all the proton transfer steps. / 1)NaOFL100°C N 2) mild acid work up to neutral pH OH if \N/V\n/ O “2% 9% \V , l . F l .1 , for A? 9,1: #90 CM? Why Mylar 5,14 { H 506 To MCJTTZA’L P” V . H N 1L . L) / W 0% mark F; 0% W WW7“ Cm t) t' Tris») NU Chem 210—2, Winter 2004 F inal exam 6 Bonus. (15 pts) The Curtius rearrangement is quite similar to the Hoffman rearrangement. Propose a curved arrow mechanism for the Curtius rearrangement of benzoyl chloride to aniline, as drawn below. Show all the proton transfer steps. . 1)N N O? 2) H:O,3heat @250 , /13 / (9 MP. M u! a” o 05" If M 14.7} ‘ f9 \\_/ t+ 4:1 {if - ~ r—PL we 0 Dirt” 'J \ D7 (4 L“; NU Chem 210-2, Winter 2004 F ina/ exam 7 5. (20 pts) From benzene and any carbon-containing starting materials with 4 carbon or less, propose a synthesis of the following molecule. You may also use PPh3, the Swern reagent (dimethyl sulfoxide and oxalyl chloride), NBS, tosyl chloride, pyridine, PCC, mCPBA, peroxide, and any inorganic reagents. NU Chem 210-2, Winter 2005? Final exam 8 6. (20 pts) From any carbon-containing starting materials with 4 carbon or less, propose a synthesis of the following molecule. You may also use PPh3, the Swern reagent (dimethyl sulfoxide and oxalyl chloride), NBS, tosyl chloride, pyridine, PCC, mCPBA, peroxide, and any inorganic reagents. Hint: Think Diels-Alder. (a fin OX0 5%; wVMZXLT A I a V M“ l i "i WW; i, \ D ‘12:? M f M; 9A»fo (7‘ Z g / WWWWWWNWMM} I / ‘W/ (0 Wm WM M a . Wkfl mgr, ( EM %( W @/\<0 6%; W {M 0 “"4 N wag W:ng f ‘ i“ L LN of Hair; ‘‘‘‘ 1&3”: “‘9 N M3, Q“ “j {M LWQWJ “f l/ i ll AMT/C“ Wt @6044: “'r/“r/ 5’3?" Z WAflwauTi H OH , c; 5” r w W M /fi- W A. Of! M M M7?) fl“ is,wa M MW w (Y Z [ E M g «kW/W M/ all: mm v V» W m m . A k g AM M4 , 553” Mm avg/WWW) N M, 1% MAIN fie l _,/L~/ My») “ "Mike r’// < (IF/{95:} W V Mr £ V W {l a, (gt. i} ’ “WWW”! { if}? 0 \ij/ n 24¢) ‘ Maw” R» (“f 2/ :1 {a {W (d6? «W/ \ W” W Mex, JL TaO 14 CM ’ LT M w wwwwwwwww ~ U «www/ n7 9;? WM kfifill”? XMA lira/i > am /, O ' ,, J M L ”' “”° 1 lawflaél 930M W Va 24$: l Vfikwm)f§ W05 ’l ' g; WWW W {my ‘ 3/} 575m} [3 WWW] NU Chem 210—2, Winter 2004 Final exam 9 7. a. (10 pts) Using the polygon rule, draw an energy diagram for the MO’s of the planar cyclopentadienyl anion and the planar cyclobutadienyl dication. (There is no need to provide the lobes.) Fill the available electrons into the molecular orbital levels and show their HOMO and the LUMO. Are these molecules aromatic or antiaromatic? _,a F.— t/uMo lp/V 4a— WI [rt planar cyclopentadienyl anion planar cyclobutadienyl dication b) (10 pts) Draw the HOMO and LUMO of l,3~butadiene and 1,3,5-hexatriene with atomic lobes showing clear demarcation of nodes. Use this information and any necessary diagram to determine if the thermal [6 + 4] reaction between cis, cis-l,3,5-hexatriene and cis-1,3-butadiene can occur. What about the thermal [6 + 2] reaction between cis, cis-1,3,5~hexatriene and ethylene? (You can buy the structures of any (or all) of these molecules from the instructor for 1 pt each if you don’t know what they are.) NOT glide/24y NU Chem 210-2, Winter 2004. Final exam 10 8) (20 pts) From elemental carbon as the only starting material, propose a synthesis of the following molecule using at least one Wittig reaction step. You may also use PPhg, the Swern reagent (dimethyl sulfoxide and oxalyl chloride), NBS, tosyl chloride, pyridine, PCC, mCPBA, peroxide, and any inorganic reagents. You are not allowed to use Corey-House in this synthesis. Hint: Think acetylene. NU Chem 210-2, Winter 2004 Final exam I] 9. (20 pts) From any carbon-containing starting materials with 4 carbon or less, propose a synthesis of the following molecule. You may also use PPh}, the Swern reagent (dimethyl sulfoxide and oxalyl chloride), NBS, tos l chloride, p ridine, PCC, mCPBA, peroxide, and any inorganic reagents. /; (A A ,~~/’9.L W I, x o / 't (r v, (I l, ’5” to) ,0 ‘ t/ O f> ti” NW/z’lj/ _, r i / 09% t1” 2/ K Mw+ \ 4 0H 0 l A M 5 ,. co, ,9 to; 2W , "wiij \H/ H ¥}I@/\/0 H Vic/Gaza _,., (a p_ a V H f, D as W 3 p; f / it ("ON ,0 r\/ ...
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FinalKey_Wi04 - NU Chem 210—2, Winter 20“ Final exam 2...

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