Summer 2003 Test 2

Summer 2003 Test 2 - Chemistry 223 ‘Tésf 2 ' _...

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Unformatted text preview: Chemistry 223 ‘Tésf 2 ' _ 'Summelii, DI. Wells. Scare = npscan x {Ti}! 13} + 13%}; E complementary cnlnr color x{?flf13):30 —@ IV. .I ‘35 {ft TD J‘. Name these compounds wiflmut using the word “banana”. (5 points] u~methnx aniline Twm aways follow Wfll‘th 1G points each. ESSAY 1n puinm. When (H)-2-uhlombutane reacts with benzem: in the preéenc: ofAIClg catalyat a scalcmic mixture. of ifinhutylbfinzem is prnduced. That is 35% {R}-2-phenylh‘utaneand65% {fl-E-phenylhutane. Explain. What is the origin nfthe scafemfc mixture? H E: s?“ \C‘JMB M Li £1 e E 3 AlCl "t" \/C—CI —3—'- ‘r’l (Lilli H Jr J m 1 I 5, m 55 5 a WEEK? mfi““ ‘4’ / flaw—#fiwm "‘fi (.65 Cl-Ri—rq I} m 1.4. L“ I EJI: Legit: dxh;Z/hu.fi¢ whisk-j £4]. " / Wth L/ La; IA? +""L Legal) Fflfi; .LLHNUJ 14: +1.1 E8) I); Aymara-rad 113.: a *r'mc. wabaiflmfi'Hfi (ghnmr) 3Tb; ah Inurwbhifi“ (a. L; Mil-WEE Yfifimfllr ISIng we. wane-15$. (new, (sylfpnmjr twamm ran-‘rwt Sbm ([1) +' Sflgbéj' V Bywaé an 57"“ Fméhfir 3w.“ +¥we +11: E® x5 Eda.) dammg k9,} b» 1m E. E Jrhx . -- Wed.) Grm“\ flhww \EJ we; Wan-Ill: flj—thj'l- CI“- finflr-JL { Hm}? ESSAY lflpohfla Consider the ele'etrophilio aromatic substitution of methylhenzeoe. Draw the arenium eationpioteunneciiaie and reso_o,3_nee sh'uetures that result from meta attack and para attack ol'the I'Ci1 eleetrophiie that explain the experimental observation that the methyl substituth is not a meta director. but is a para director. Be sure to label your drawings and use words in your explanation. CH3 “43 C541: LHJ u + a: m g—EGQ C__;, (a meta attack H fit at H G) H H gram—J}; mm“- C’JC— EJ’JF'FI‘QZIFiIF'iE ‘3 Her @ iflb‘si‘nbiltlged 10,.a athkm Aha-:93 éamlh’u“ at? H.3ri'wi . CH3 1 _ Which graph hEiDW is the must accurate? '- aromaticitw amm aticity '- .- ummalicih' aromaticitv 1 l 3' 4 5 {a 1 2 I1 2 . The hydmxyl group {—DH} is an (inhor'para directnr because A. it is: an elm:th density withdrawing gmup B. it is an t‘lEflfl'fln densiiy deflating gmin ,a— C. of stories b D. of induction (E) (if reso HERCE Ln! 1'! 3 . fit. ten-botyl group is an 011116pr3 director because A. it is an electron density withdrawing group 3'1 @ it is an electron density donating group i,- 67" _ _‘ ‘ -- Cl) C. of stories 1; r? ‘ D. ofrnductioofl- _ ram—u Lt: all 1.9% tr. t} flee: Lani. a? j E. of resonance 11 4. The low yield of the ordro substituted product can be esplained by Clg {'1 FCC-13 h + + b Cl 5% Ices Cl 35% A. the nonplanar benzene ring of the reactant El. considering the “paracearchiug” ability:r oi" (11‘ (E) considering the large size of the tert-botyl group D. resonance stabilization by a lone pair E. the inductive effect ofalkyi groups 5. Compound 5 does not undergo DieIs~Alder reactions with ethane because _ @ Lhe s-cis conibrmation ofS is not obtainable V” . compound 5 is aromatic a) C. ctheue is a good lewis acid I). ethene is a good Eeaving group Li. electron deficient dicnes are not reactive ‘l'J'I 6. Molecules with extensive conjugation absorb longer wavelengths of light because _ ® the Homo-Limo gap is smailer I E. the l-iDMO-LUMU gap is larger u\({ [7. nonbonciiog electrons more to hi ghcr energy Y it i). sigma bonding becomes weaker 7. The most likely product of 1he following reaction is _ HL‘l ——I-. l 4% LII It LI-L' C] l! " ll Cl . H q l“ C] U Y”) K} a. La") {1 n E E . The most liker product of [he lbllowing reaction it: _ c133 CH3 I + Jl/ “h l CF; en3 [3H3 '31"; we”l ‘31"; {_‘H3 [11:], 9. If [he dicneophile in qucalion 3 was replaced with Hamel . l ,l .494.4-hexafluoro—2-butone the reaction rate would :1. increase . u f H a do! a j no “' {13) decrease a l3 L l .I I—l IL"! 1 .. I -r I l""- II. R L. l‘Cl'flfllTI the same :HL .‘ gar-4 4., x c.» tie-1 1 L.) 10. 1|.‘Ir'hen an organic moleeule absorbs visible light {2-9 an eleetron is promoted to a molecular orbital of-ltigher energy I’ll B. an electron descends to a moleeular orbital of lower energy l‘l C. molecular 1rilza'ations are energized [1 nuclear Spins are flipped 11 . Ripe squash appear yellow heeause they _ A. emit purple light :l absorb purple light (H) C. emit yellow light D. absorb yellow light 12. A 23.3 gram carrot was drier] and ground to a fine powder. The powder was extraetetl with Sill] rnL of hexane. In a Ltlfl em sample eel] the hexane solution had an absorbanee of 1.6] at lambda mas. The molar mass oi'B—earotene is 536.39 pfmol and its molar absorptivity is 131$th liter a“ moi em- 1|What is the percent by mass of B-earotene in parrots. A. U.US4D% a. tlflltfi‘ifa Pr 3 EL l- " m g. {lessee .. {penises/s C : Pr _ t. LI 1 |.a| in" soil Cl :7 _ l’saew LL“ mam :- - LP N's—w Hull "_._ Mani Felt-IL . Q” _.__.U' :- eas- “s. L. i"'“‘-~-'a:r '2 frog $l.t.’:i_i" I'm-"t & BL'Eci j 1 qufl '5qu g I. Maul ma. souls we’- a 0 ‘9: ems-e EL”:ij Good times . . Look of The reaction sequences below for questions 13 - 13. easerne: atel3 C]? Fat-h // [3 —-n»' 1.1 Ct-tflltC‘ICE—ts r sect. H CH3? H1? “3'3 l i BU; ] _ . _ fl \\ ratios.razsol alsoi -—-——h-— If ——p-. “i 13. Compound 13 is most likely _ Cf Elli H Ell] Cl—Ar-Cl CH1 en.—e=o ‘Ow 14. Compound 14 is ITIDSI Ill-{Ely 111 ['1 i 3 H H [KN HCH % l l I 3 CH?r . .' CHl—C—UH SHE—:13 CHE—[:0 (“-5 \"i C! (*1 Fe L1 15 . Cu mpound 15 t5 magi likely . C1 CH; CH; CI L; I | | CI—i'-‘ra—Ci Cll3—{J—C‘E (“Hr—FC—H ["HgCIhCl-h L‘I-h—C—CI—lq @r 115. Compound 16 is mus! liker . CH; CII CH; CHw—C—Clh CI—Fe—C] CHECI-TgCH; CHECIMTII; [wk—y—H H1 © 6? CHa—ili—CHJ {THECE-IJCIIJ lie—CI ills—F—H CH3 CH3 {3| CH; 17. Cnmpnunc‘i l? is mast likely 01 N03 N03; 303}! SUN: "\ 13. (TOmPrJund 13 is must til-{ct}! 02 ‘02 15031-1 HOS NUS affix-II. . “a . 030$ 059033 {J 50311 05031-1 USU3H ...
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Summer 2003 Test 2 - Chemistry 223 ‘Tésf 2 ' _...

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