exam1key - Note: Read all questiens carefully and answer...

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Unformatted text preview: Note: Read all questiens carefully and answer eeneisely'. 1l’nu may use molecular mnrlels during the exam. Part I. Multiple Cheiee (El) 1st} Cirele the lettereerreepending to your best answer for eaeh el'the {allowing questinns. 1. {5 1115.)"l'he fennel eherge en exygen in climelhfl ether '15: [A]. -2 CHJnO-CHE, , . {B}. —l @e gnt’quzaw-szo (m. +1 2. (5 gate] The TUPAC name for the fellewing eempeund is: r-—__ éll (fl—'3 { {A}. iii—trimefilylhexene CH3 ECHE II I - ‘ . . 1 "_"l—— l @ 2,2,41ramethylhexene lCHs_C_CH2_CH_ CH3 (C). 2aethyl—4,4—dimetl1ylpemene I l :L . CH3 {D}. 4-ethyl-E,2-dunet11y1pemane 1. [5 [Its] Cl'l3tjl—IA*U"CIIECI{3 and LTl—ljflll-lgCl-lgf'l-lgfll-l are examples of {A}. reeemmee structures LB}. unantiemere (ff). eenfenueiienal isemers @ eensmutlenul isemers 4. :5 p153 Which ene of the underlined meme ix Hp? hybridized”? a I'L' rm. Betl'lw LIE-- fie F-CF (“ . NH. ' PM: " ‘ [ ll — ' H (+3131?! Lil-'3 :D}. ml.- e '-._\________.-" f | (T. 13-7) - H - “IE F F Iv fig- H .I’ 'I, 5. {5 ptsj 1'-.‘-r"hieh conformation represents the most stable eoiiliimiationHiggins—1,4— tiimetliyieireloliexaue‘? .r-I—‘1I‘-- ran as] til {j m: m ti. {5 pts] Which of the following:T statements about eonfouuations ot" meLliyleyelohei-taae is true'? eHJ :fl\ 8 etaJ gt a, {It}. The Two forum are in equilibrium and are present in equal amount at room temperature. ( '5? g {E :90 nef— Amtg 544-5 time Mgr/g? ) {H}. The two forms are not in equilibrium. The two forms are in equilibrium but are not present in equal amounts at room temperature. (1')]. The eontbrmer with an axial methyl group is present in a larger amount than the equatorial form at room temperature. Maj CW? :35fo I; x, :7 .1— f-erfi 531253.? :2“: Jess Jensen-u? ; F. ['5 pts} What iritermoleeular force is strongest in Cl-Iifll l? 6.9.]:le l-lydrtigou bondian {B}. van der Wat-11s [C]. [Dipole-Dipole {D}. Jon—Dipole 3. [ 5 p153] 1'i’i.’hieh two eeiiipeunds in 1h: iiiltnwing pairs; are eiiaiitimiiers ei‘eaeh mher?‘ [ll-IRISH1 CHZEHG I; f ‘1.” Cw\ imd Runs] (“I I Br CHECHE CH30H2 Bf ’2 r73": (Ill—13 e I: fl-illflr and NIH“ H C" H Elr Hat H H _:_|:lH __ _. EC“;- H‘y. (0.9% (TAMI H H H H (D). mm m emy<j flg7£ Cgffa/é H CH3 CH3 9. {5 pie} which ef The fellewing is 4-[1-I11fiti]}']-§jh—Fl:IQ.5-dii116th}-‘l]'lflplafllc? We?" | R l a H}. [5 pie] SLi-ueiuree K and V are etereeieemers. They are not superimpesable and are iiiiri'ei' images of one enether. What best describes the relalimiship between X and ’1"? {A}. DiaHEErL‘ CIIIIICI'S @ Enaiitiemers {C}. They are meee eempimnds. { D i. Ennibrmcrs Part [1. {3D pt‘s'} Basics 1 I. {IS [1th Dutw three IESHTIHHCE structures i'ur eurhenetu inn. Cit-1". Using curved “eieetmtt pushing" arrows to help j'flLi with [anti tn 3hnw} hew theee TL‘StJl'lflE‘lCL‘ atruetttres are interemweneii. C: E;- or 1:3" l (L 6—4? C eu—r‘? I”; \h . / \Q 3’? \ G U -x' c; U 0 ‘— § {27% 5 I'm $4971; 12. i 15 1115} Based [in yeti? "ehetttieai illllliiiml" and tit-hat ynu knew of eieetnmegativitieit. Sheri-r the directiett ef the dipstie memeitts Eli-U11: t'hilewing bends. II,r Draw arrow from the positively charged [0 the negativer charged end). ch—Ct {'Cl-13)-3C=O HO—H _i——~> -+-—3e i—‘t‘ gflrfg I‘MFLS 5—9071; Part 11]. (HI pts} Nemenelature I}. {111] pts't Name the titlhwwittg eempitund. 2mm} L_l/\ :er1H .- a”; a i t , i 3 - K— (Ninth — 3 e- five/in '5;;}L'o/-'2E t i 77L” I" L «(h— Ur ,-—- lw' _ n; :_ fine _____ J" if I HI JI | Hie- r 3' -' 1! I I I): r1r_. J-II}_' I. ' -'J 14. {ID pts} Draw the otrootoro of2.E.4.4—totromothyihoxono. - I I {Chim- fiv’bw' '9’ . / 4 [its \<, k?” ff” y'all i 1/3,, 3. 27L CdWFC% flagr'fl'm Elf-flit; Part IV. {3mm} Conformation {gaf— _’ 15. {H1 pits} Draw {1'} a Newman projootion i'orotoio and [2] a 3—D porspootivo drawing, using wedge and dotted (hash) bonds for the most smhio conform-or oftho following compound. “i. _ '_'- Ct) oH H CH5 (:1. 3 :5 _F H 1 I H H \ H CH-d—C o—oH3 C H1 :3 3 + i i yaw—R H d 3 H 4/ at CH3 it 3. . _r_ _ I # H {#3 H '91—- almw ‘3 ID if m I; 5 Fmgféu S |"' _.r_- LHI Ti). 2 lti. {20 pm} Draw Newman projection fomtoio for the anti. gauche- pmiaity eclipsed. and totally eclipsed oonfonofirs at thoir oorrosponoing lootttioito in the torsional onorgy I (I I If; f- r- C + oiawrom otrhotoito.E H3 Ht 1 H3} 1 4+ dam} “Elma” [-I fifls \ E {gfiB/MQU log; PFPWM Pa rt V. (4'3 pts) Stereoehemietry 17". Ht] pte] Considering the following eompound. {i} lttentil}; all stei'eoeentera [eltiral atoms) on the structure helow using stars (*1; (ii) Draw all the Stereoieomers; {iiil Label am; one Limit one is enough} of the eltiral carbons in anv one of the otereoisomers as {R} or {S}; and {it-ft Identify all pairs of enantiorners and diaetereonters. You may use Fe B, ete. to label eaeh S-iltertJlSDthfll' for eoiwenienee to answer question tit-'1, ' t . l ~ I L, f; If gr g‘P't'g LUI’CIDLE Contra.” AIL ‘43 F RM. i “Tun—rah A a“ leach greed“ r: “E r I) ‘ ll 5253,5636 [LE-Hip!“ __\ I, ' PM '! x 4 Warn Part VI. (Ifl pits} Bonus liloji'fn—Lr—“4| 1| XE— _ “er”:— 1 3. {ID pts. harms} Draw a reaction—diagram profile [Lea energy as. reaction eoordinate) for a one—step exothermic reaetioa. Lahel the parts that repreaent the reactant; prootfia. trELttSition State. aEllk'ettiOLlfllEl'g‘y, and heat oileaotion. 5“ flange-an Seth: {T5 _J ,-_‘_t~‘af1t“‘etWi rlfil 'i xx _ _ __ .._ II I _ - . .(2_ p4 J; r 6- Lt' — f [3+ 5 f '. __o_e :1 exit WA“ W ” J l q“ i. __ .H' I -_ . J . I __ i I fl 1*] Eur.” 'T i" are e-Tr c Vil :- _r r’ r Vii (:36? w r| ‘ I“. ,.. b. ':-'?’L'H’ ‘2! {flit * 1 I ll? .J'u. ‘3’ III . r. Rte-Mutual. VG o'i H r. l.— i ...
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This test prep was uploaded on 04/18/2008 for the course CHEM 2301 taught by Professor Gao during the Fall '07 term at Minnesota.

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exam1key - Note: Read all questiens carefully and answer...

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