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Spring 2008 Test 2 - I Chem 223 7336 2 Name Kai Dr Wells...

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Unformatted text preview: I Chem 223 7336 2 Name; Kai Dr. Wells, Spring 2008. Score = opscan * 82K20 + essay: * 8200 + 2 = 7L (nm) < 400 425 470 520 570 620 680 >700 complementary color color UV Violet yellow blue orange green red yellow violet orange blue red green IR Useful Equations: E = hv = hc/k h = 6.626 x 10 '34 M 0 =3.00 x 108 m/s : M A = 8C1 = abc LJM I THE 5(‘bre / {S imC/Vjfiwk . Essay A. 10 points. Using the p-attack of Br+ as an example, explain why the amino group (—NHz) is a strong activator and orthofpara directing substituent. Show the mechanism for the formation of the arenium intermediate, its resonance structures, and the resonance hybrid in your explanation. ro- | _, MN; :13?“ N M M" Tl e” a“ I ebb 59/eaok Cuba") Essay B. 8 points. Ripped from today’s headlines . . . It’s news of the week I!!! Read the article about the cyclization below. Then answer the questions. a n bho . r s curSO ’ \ flighodiagte {tom ablcydggfgfsor’s com— _._-—-r--#""'”- ‘H'r' i :‘dcarn believes that tlmtie reacting diene '1. -c blTlflgS 01110105 T30M ‘N ~ pact SYNC“? oxim‘lt‘f and 9‘ (:YCL‘zA RTERS d. lkex-lcm‘io P“ t . . .- {thercsult- I. an *1 . t v. ‘ 11d'utYO CLOSE- QUA d the cycumuon- Thu“: _..___.»"#Ef\ ._ - elyust ' -- udcrreacti \ . 'th Dick-W .. sfot'l‘fiflt ‘. U an ‘ — 31111361": forms 811"“ ated diene ‘31 \T 311 BUG-3 “‘3 - 31115:! 1“ l. conju‘h'. frc quC m“ r ) YCHCL i t“ x. h ’ h ' :I Cfltfl‘fi-rbts 01 _ - .._ '5 around the carbons of the diene and put squares around the 0 On the molecule on the right, compound Y, put circle; carbons of the dienophile that undergo the Diels—Alder reaction. : o What does “complimentary electronic properties” mean? I’ L a e” POCW' dib‘t’. fern/“'5 {fink 7 IIIIOR “3*” 0” nun amoeba amt ‘ e:- (ft/W CH— (C/Lusc') (OHA1\7 H 1 . From the cyclization article: The UVN is spectrum of compound Y has a broad “hump” centered around 175 nm (i.e. Km“ = 175 mm). The UVN is spectrum of the product would have A. a peak with Xmax =175 nm B. a peak with 7km“ >175 mm C ©a peak with Xmax <175 nm ,— la 5) QMS“ 7‘. .5; fin £\,\ 67m 1...} my D. no peaks E. There is not enough information to determine. Ska” ‘l‘Y ?\ - 2 . How many constitutional isomers are created by the monomethylati on of tetracene? This means how many possible products are there in the product mixture? A.l B. 2 _ C © 3 D. 4 E. 5 tetracene 3 . 1,3-dime1hylbenzene is also known as A. parasole B. metasole C. acetophenone D. para-methylanisole ©meta—xylene l? atria? 39 4. Erich Hfickel would have most likely said “ A. 1 can‘t believe that Joe-Joe ran away/.8 B. Sterics causes attack on the other side C. It’s the water that leads to the second reaction D. The kinetics prove it’s first order The mber of i electrons must be 4n+2 <9 nu p . . E are Mach) #3. n: l ’L 3 “l LIW+L 1'. (9 {O 5. The nitro group (—N02) is an meta director because ® it is an electron density withdrawing group \/ B. it is an electron density donating group ;( C. ofsterics st. D. ofsolubility k E. of resonance 3L. Big Time fun with benzene for questions 6 - 10. Big Time!! «amenr FeCl3 CH3Brf AlBr3 + /———-—->- —h- 2 l ms 6 @o H/ \CI 8 NaBH4rH20 9 V! o \\/0’H . L Cr03 facetone 1’ H20 0 10 6. Compound 6 is most likely Cl 3 . Compound 8 is most likely “036” 5 9. Compound 9 is most likely a o i” 10. Compound 10 is most likely 0 OH O l 11 . Oil ofbitter almond is . o~. ‘9 i — 3913" H 8 «a: / oi {DH 0 H] iH 0/ oi iH / 12 . The hydroxyl group (—OH) is an orthoi'para director because . . i O - A. it is an electron density withdrawing group L3) B. it is an electron density donating group _ C. of sterics - ' D. of induction - - ' (‘9 of resonance 1 3 . The low yield of the ortho substituted product can be explained by O O O 0 g E E t H H / H / H \N/ \CHS RN \CH3 a.“ \CHa aN/ \CHa Cl+ CI —I- CI 2% "3% Cl 91% A. the inductive effect of acyl group ’1’!“ s) ,2) £5 fl L) t w - C. the nonplanar benzene ring of the reactant D. considering the “para-searching” ability of Cl+ E B. resonance stabilization by a lone pair (5 considering the large size of the acetamide group 14. Compound 14 undergoes Diels-Alder reactions with ethene. While compound 15 doesn’t react with ethene because . Loo kn} {a 5 -47....) @the s-cis conformation of 15 is unobtainable. B. 14 is too electron rich C. 15 is not conjugated D. 15 is aromatic E. 15 is not aromatic 14 15 15 . The 13 C NMR spectrum of 15 would have _ lines 16. [10]annulene is not aromatic because CE it is not planar B. its lone pairs are perpendicular to the plane of the ring C. it does not contain a Huckel number of electrons D. itis not cyclic E. it contains an Sp3 hybridized carbon 17. Successive nitrations as shown below become increasingly more difficult. @th NO2 N02 (5 OLE? in i it {7 The best explanation for this is . 7 A. increasing steric crowding rm") 5‘- . Consider The UV/Vis spectrum of act/1'4 for- questions 18 and 19. r9“* N02 02rd —.... ® increasing number of electron withdrawing groups -—- C. increasing ring warping «x D. decreasing conjugation g r w.» \(XL‘M’L 18. The n ~> pi* transition is at A. l6l B. 187 um. I I l 161 187 220 A (nm) it /C\ H H 19. The hump at 2?0 nm is due to Q a forbidden transition . the deuterium in UV light source C. absorption of the quartz sample cell D. switching from one type of monochromator to another E. sigma electrons Formaldehyde 20. Which one of the following is not aromatic? 270 I D5“ 297 ...
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