Example Final 1 Key (1)

Example Final 1 Key (1) - CHEM 223 FINAL p. 1 KEY sec (32)...

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Unformatted text preview: CHEM 223 FINAL p. 1 KEY sec (32) 1. Provide unambiguous names for the structures shown below. Use stereodesignators as needed. 0 2 ii 9—0 J! K V 3—daer f— $1 é; Hsnnfna "/1 Q 96/2?!” fan 0/1 a f L 5 q 3 L COZH ' (312)—25-d7meéh I—3-eHr /-7-Ae4<ene 3—-a¢.oc c/o en {—ane caréox //'c 5(- 2flem amt/v ’0 S H . 4mmve a,” [S 3 5H , 2 l 32 S J--5—L_€‘fi:¢rF/4¢¢ \ (33)"3-ch/ar¢—1—m¢£‘h /- 2_me{fi’y/_ /_Pro Wig/2% N. Z faclOProfgnc V 1 no'l- Ma N32. 0 3 cozH xix/5w 5 ' ' ’5 CI. ~5ff—12—hfé'a—5‘Ch/oraéen ofc acfd Ll CA are 2 6a anon; 6 . . . (2]) 2. Fill in missing reagents and/or products in the followmg synthetic transformations. 0 (o dad/1 / ‘ é H30+ / \ or H3+L /\ Ho “a o NHVOH O 1' @“V’OH H 50H 2. H3o+ jut: +}OH \___________________-_J QP‘ES lac‘H/t Or D/L tLIT‘E-S ’X‘Y‘am:~$%e.reo CHEM 223 FINAL p. 2 KEY sec (12) 3. What kind of reaction is the one below? Suggest a mechanism. / Me M‘ M‘ ameflt l @on m, K G91.- mech k) % C6 Zpts (Wit-1+“ 1- ‘ : Carbocm—han/ (10) 4. Diazomethane, CHZNZ, has both hydrogens attached to the carbon and a linear C-N-N skeleton. Draw its Lewis structure (with resonance structure(s), if required). H + " H — + \+ '- \ — —__ a. \"—- Z , H /C—~N—-N'. H H/C ~~N' / \\N:.. r' 7P+s b‘j ‘ 5 +5 " stzl¥ 4 ~ ~ ~ ~ O ‘0 Picaéif. éjff‘érc/f: (10) 5. In biological systems, NAD+ is used to oxidize and NADH is used to reduce. For the following biological reaction, show how lactate is oxidized to pyruvate by an arrow pushing mechanism. H [a Base. H H R I \9 fig k R ' wea > + + b N/‘/ H O ase i i w ' ' N. R l o R . NAD+ / lactate N ADH pymvate Correr answer : uP-la 764—5 «For somehow McLFcA‘bl'n Wat NAD+ @l‘cks 0.? 0~ Hjbir’uéc (mo't‘qfrabanb (12) 6. Rank in order of increasing basicity (1 is strongest base, 4 is the weakest base) ZPJt-s ” ‘ ‘ ‘ ,‘ tBuO- CF3CH20- C6H5OH tBuOH . / ll .3— ...L .5;— .._§_.. \\\/\ Mkbms e r- 3 \/J L‘J less available—— arrec’t H (a, EFL: SF’ES CHEM 223 FINAL p. 3 KE ‘1 sec (18) 7. Designing syntheses. You have the following organic starting materials available. cuscuzcuo © 5:0 cu3cuzou You also have NaCN and any non—carbon compounds you need. Now design syntheses of O Q“ sod; d/ CH3CK1CHO T417 CH3CH2COZH “fl CHscuzcoa O 9 No W @V “Iggy ’- stvq \ {013 (~3 if-arcier reversed) our‘) TS CJ Pfir 0" W3"; 9 (143042914 1:33;» m3wzgr aw: 0“ Vk‘ IQ Br 2. R’Br "z (16) 8. Indicate whether the pairs of structures shown below are conformers (C), enantiomers (E), identical (1) or diastereomeric (D). It is possible that more than one designation may apply. on 9“ a cuzou c 0‘20H q a» 0’ Q’ __E 9‘” 5: CHO w ’ H q I») ' Q- SD C: c) fl 1):. M E i C CHEM 223 FINAL p. 4 K5 V ' sec (08) 10. Here’s a reaction that works very well, but that you haven’t seen before. The aromatic bromide is dissolved in ether and the rest of the steps are done sequentially with isolating the intermediate products. C02 is carbon dioxide, a gas, which is bubbled into the reaction mixture once the magnesium metal has dissolved. Show how the (—COzH)-group becomes attached to the benzene ring. a ‘1" 0 2.364 col cuaor 3 3 H 0" + M ° - 3 3/ :6 ; ‘ V) HSO I OJ} C \ C1430 / MflBF g\0©,/, \b M20>//\\(2\O o \ \ (J4 3 O \ / Mao V M- . ‘ 2?“ é; 1c; ca 15 ltiua C10 P Z / (12) 11. Underline the species that dominate at equilibrium and provide a rationale as to why this is the case. NHz OH NH3+ Q- + [j 24 j + O (00 ‘t7 PK“ = . ‘ 4-H m It (possible. Vfi'i'tmalzxz " [A 3 at: *Uz S‘L‘Abic acich Wm space, 9 U h I' ‘ . ’— - 6“ WW “W W - “tartscffiem (06) 12. Which alkyl bromide (below) reacts faster with NaN3 ? i G k) hm NH; 3 Br (06) 13. Show what an allylic cation is — use a specific example. MULch be. a / H H \ ¢C + H ACHL \ 'l' out] 4H3, Lui—H/toud‘ resommca A74 K CHEM 223 FINAL p. 5 K sec '0 (13) 14. What’s wrong (or right) with the synthegiCWelow. .mco W P “H b ta 4 PES 0“ ‘01 p ‘ 0/ an, O: “k”; «l r M OH \Hzo y 3., 2.cuscuo “""’ «matccnrvrlzct but 3P,“ “K NH O CH COCL OK -————=-"°‘°°‘ 1‘ —-—'3 ‘ I-izsoq Ala3 Shoul55° N02 \ +ao deacliuait-QANOL a)? 4P£S [B rMOZ fiamL@ (10) 15. The structures of benzoic acid and perbenzoic acid are shown below. Based on these structures, do you expect perbenzoic acid to be more or less acidic than benzoic acid? O O 5 ts correcl.‘ O ’H / ‘ ’°\H P answer , , \ PK“ 4.7 PKas’a 7’ h —-H* [ O o _ 9 l 0 ‘\ + l 9/) / Can N : \ i \ .. ’. be Y‘Ai'male.’ clalOCAlié/cl (10) 16. Provide a mechanism for .. " / ‘ NHL CHSCHO 3+ H20 CH3 \ A H Esra H ' H 7‘ .. ‘ ©flde / filc/ 3 ohm. V“ \\ 1‘ - adclm 0“ K___, 4,?{3 gr some. le—mcl (06) 17. What does hydrogen gas with a platinum metal catalyst do? Ht. . _._—~\:> Ydufies &A o A'i'ro 14> C2C Pk &mbk lwéjl 0" Gad: ...
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This note was uploaded on 01/19/2012 for the course CHEM 223A taught by Professor Nielsh.andersen during the Summer '11 term at University of Washington.

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Example Final 1 Key (1) - CHEM 223 FINAL p. 1 KEY sec (32)...

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