Chemistry 3A - Spring 2000 - Frechet - Final

Chemistry 3A - Spring 2000 - Frechet - Final - Chemistry 3A...

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Unformatted text preview: Chemistry 3A - Spring seen Fina] Prefesser Jean Fréehet Teur full signature May 15.. 2mm Print yeur full name :LaI-t rune. First nan'le. Illrldle]: ‘r'eur SID Please check the seetien number and name efyeur' esrml. ___‘|'Ei'i VerdugeJJewn _EE1 Hamanlliristina __‘1?1 l-{icppdchn _3‘l"1 Hecl'ILEtefan _1E‘l Berthafihnstcpher ___311 SaxenEliane _1Q‘l FujdalaJ'lZyle "321 BeetsElrian _11‘1 Watirinsfinegcry ___451 PurdyJ'u'letthew _121 HIEdtWEILBEthEI‘I’f _4T1 EuanaJahn _131 Feaflaniel _Il‘l1 Hellandfindrew __141 Werkemafiuen _421 Duncanfindrew __EE1 Feterltaflarcy _431 Trimhtefilexsnder _2T1 Leeflharlea ___5‘1‘1 Marceureilcfiaa _211 Tripp,.lennifer _52‘l Jen.l.ll.lend'_l.r ___EE1 Fadiliaflmayra _53‘l Lingfranlt lfyeu are melting up an l-grade. indicate the semester yeu teelt 3A and the Prefeeser _ DH "mm In fill: Bax- This exam has til pages; make sure that yen have 1" 115} them all. 3-. 119} 3._ 115} Please be sure ta use the gag: usefirl' data 4-. [15} given an page H. 5-_ .1115} s._ 11?} We will enty grade answers that are in the 1‘ —-"{1 91 designated spaces Please dc year scratch werlr. en a {1?} the tracks at the exam pages. 'll'll'rite enlyr gag answer in _ ' each emblem; multiple answers will receive E rilreriitr s._ £15} even if ene cf them is correct- 1'1. 115} 1'1 __ 119} Hate: This exarninelien runs far a. tctal at 130 minutes- 12__ 3:15} Me questiens will he answered by prcctcrs after the exam begins. Please write legihty; ambiguous cr messy answers will receive Lead“. Tcial' {2W} filflflfll .J.III.J. Fléti'let. Elvtlrltaileyl1 GA T5 GED-IR] J.M.J.Fl'&[=l'lfl'l. Elm. ml. Chant. 3A May 2WD. FinghExamihaflnn Page 2 pf 14 t. [15 Paints] [a] pmpttse a atmchna for an alpahnl piifla that has the fulluwing 13: HMR data: “HEII‘I'I‘IEI' [praipn damuplad} spectrum: peaks at 35- + 19.1] 31E and 59.5 ppm: DEPT-Elli]: E = 31 -Eppn‘l'. DEPT-135: puaitive paaka at 3 = 19.0 and 31 .fi: I'tEQafiura peak: at E = 69.5 ppm E I'..I'-t' "t'aur answer ahauld shat-t — '. . - . a clear aimcture __l|'..f. L”: _|_ . 1-1. .- _"'I .-'\-"I 'l - L I I '5;- Dr' II {in} A hydmmtlrhnn has the formula '3? H13, it exhibits the fuliuwing speclmsmpic prupertifls: IR: pflalifi at EDTE. BEIGE-EDDIE]. 1649 and 333 cm"; 1H NMR spectrum 3 = 1 .3 (m. 2H}: 1.? {rm 4H}; 2.2 {m, 4H] and 4-13me {:1 uintet. 2H]; 131: NM R: E = 25.3.: 23 .1"; 353?; WEE and 149.7 ppm: hydngnalipn affords a product with _I11E farmula CTHH. [Hatfim mEtans "muffipiafi [i] What if what ia its degree of unaaluraiipn cf the hydra-35mph (1-; H12? . __ {all IE6. 5-2.: I I "I. _ mg: FLUL, Answar: ./ at;- (it: : t:i -- {_F.l'_.'.l Lu,- {i'tj What chara plat-ism: funcfipnal gmup is mappnsihla far the IR hand at 1549 cm'i'? EH] ct- .. [a]: The characteristic IREtfieTphIEg—an my fur 1ha aarhanuuarhnn tn'pla hands pf EIIQI'TIEE- Ia: [13th me} 331mm“ man cm" 333 an“ 2120 art-:1] . .x 't. El HIM .l.Inl..L Fdehel. Barren}. m Chem. 3A May Eflflfl. Final Exam inatien Page El of 14 E. [19 Palms] {a} Draw the 1 H N l-I'ER spectrum fer Ell: HEDEHEBHa Beauming perfect splitting pf peaks- Make sure me Ieeetien ef the peeks is epprepfiate and la bell each peak. Alan drew a reeliefie step integratien. _ _—_n. 1a..—-— u- e!” {in} Sheer a fully labeled energyr dlegram fer the fella-wing reeetien H =eHL'H + Hm —.- eH GHCIGHE "‘ -. G 2 3 i rifle aw» --.+e-~I'r-T-"£ ' flue—"EH ”Er-I“ EIEDHB JHJ. Fran-2t. Bantam. EA. Chem. 3A May Eflflfl, Flnal Examinafian Page 4 (If 14 ' 3. [15 Points] Ma me Dr draw as appropriate fl'la fulfflwing mfllapul-aa- Show atarauchamistry if reIEvant {a} Lithium diiaupmpytamida {a} z-E-fluarana-mathuxy—E—pantana {a} T-chlnmhicyfibu-[Llflhunana #1111! “II J. Fm Barium. ca. Chem. 3A Final Examinafiun Page 5 af1a=i DH 4. [TE Paints] {a} Shaw 5 stap-hy-alep aynihflaia a'i H fiam cyclapantana 6 {no Mechaniarn} DH {b} Shaw a step—hymen mechanism {including curved arrows] far 1113 iaiinwing reacfian: ‘ GCI 4“ fl- -‘a- a” F—‘Jr El fi’ i r ' - ? __. “'3; REEF-fill fl —'_CF {had-“xv, rd ‘— '1: cl...- hu—F'fl a” Elf-6" 1 Ill-1 a :J ”H l. — "'__ _ affix r; 3/ - / _ [if-:5 '1“ .-..I- . Ir ' :": I'll jg? 'I- “I —"-' “MEI. ' | IKE #Ll' ir I! W [JIIK‘ H4 Fr xfl.w/:Z:hf“u . r F“ '39; -" :":} e _ 1.;- _-I:TI..-' —'l .I' 1'5".- c] Thar apiical [.‘IILJT‘EW of a sample af [Hi-E-bmmubutana la 30%. What' la its upfical ratatian given that pure {Sit-Ltlmmuhutane has a specific rutatiun [If +25“ Alan calculate the permutage af Edaamar in this aam Ia- f— 1te . . F J 6%: U'IEx-I m ‘2 @‘E— .-' Pemflntaga (if 5 '3 END JHJ. FI'EEI‘IIL'L Emmy, CA [3th. 3A May Eflflfl, Final Examination Page 5 M14 5. [15 Pnln‘ts] Shaw The major pmd ucfls} attained in the reactions helm- [In not include miner prudunls ur hy—pmduuts. Be sure in spacify sisranchamistry whare apprnpriate 00 L f m, j r” *’ I I: - It" #3” , x"- - 21 lGHanE “w a” :L- _K|J.'fi‘“ ./‘“-- Q 1} 0504, THF <31 1‘ .-" — 2] Hams-:33 .J w” 1} MCPBA in GHEBIE =( —II- il-i-fl. wall. I ._.-"'x cHon 21H man .;_{~;. LII-.qJ S HBr fl F _ —F' :- flF-fl‘f 1”... RD DR (\(r-fi'llf Elf} E! Elm J.M.J. Frau-Am. Berkeley. m Shem- 3A May 2WD, Final Examinafiun Pa 93 T cf 14 E- [11‘r Paints]- Shaw the majur pmducfia] obtained In 111E: reactions below. Be sure tn specify stereuchaml'stry where appropriate GHE .214} .x’ H C a in v.3 _ 3 will + 3 NE NH? —...._._._... “it"‘HJ-‘i‘a: EL} #5:. fiquI'd NHa # E,- / '3' Ex '95 D —'* Yam ... H 3 _ _"|_,r.'.‘:‘.'.| HaC*CECEL|$ + D (x Lam-3 ' —fi‘ / J' I (“g flag; aunt. —~ —,. a}_ G :1”- 4 ' ' a. “EU _ I'm ,4” If? 'r: 5:: a :nfluH x ----— j I 0—H” Q fl (Pr V Cl 3:1 L ‘7‘? “III HEIDAG]: in EHgflH 1|_-'| .- iymfi ————— 33% 1/ 2‘} MEEH; in CH 30H --" 3| meet: .me. Frflnmfiefleteyfin Chem. Be. Me}; EDDIE]. Finel Ese min etten Page a 131‘ 14 F. [19 Paints] {e} Fer eeeh at the res eflen sequen ees beJe-sr EI'IDW a clear structure fer the m'rse'rng tntemtstliete and the reagents used fer the seeend step. {e} Write a step by step mechanism {with all curved srrews} fer the renewing reeetien: ”leH "— . 2 HI ' {1%. __-_ Q, l\ GHa "'-. Let 1 j e I :11!!! .- a-,r .-"" _.- _.-' J's F d r I. -—- t’. :l [“3 I. _ _-'-" T x< .. r“— .r E enema JJJLJ. Free-ct. BIlIF-lltfihy. ell. CHEWI- BA May 2600. Final Examinatien Page 9 M14 I e- [17 PeintE] {a}Geneiderfl1e fbllewlng reaction: GHQCHECHEGH:BH2 ——|'- CHf—‘CHE + GHHCH=GH2 aH" = +214 Heat mele'1 “ = +fl-l1333 Heal lieg'1 mble'1 {i} la the reaetien themedyhemieaiiy feaaible at WET? Ehbw your ealeulatlen and exglaifl- {ii} Galeulate the minimum temperature at whieh the reaction beeumee fl'lfln'l'lfldyl'lfll'nifially feasible- Show your ealeulafibn and explain briefly- @636 -_.._ fl ‘L'NIH- “I; .jj. 1?? .- / {j : -: -- rife:- $332) :. f,”\/’ A I}- £7? .3 k_ {h} Wfite the almeturee at the brand beta bi mgnuehlunnafiun efMa using ehlbrihe and light. label them alphabetically (A. El, et:---i and calculate in umal retib [A : B : -.-‘,l lhe products 'will be fanned- Anewer: Structures IIIEDflD J.F-Il-J.Fr'fiI:IIIEI1.E|B-I'hfluy, CA Chem. 3A May Eflflfl, Final Examination Page 11:] {If 14 H. [13 Points] {a} Shaw 3 step by star} mechanism [with cum-ad armws} furthe reacljfln: 1} EIr2 I'Hgfl " chch—GHa. e ICES-EGH—‘GHEQ . .- 2 GH I; ' II T I"F. ' tfi‘)‘ .} . E“: I Mia-"WEI “xx-III. 3““ | I\ I LEI; —__ 152;: - I'll _ II - I" I '“H-—_ ,2“ II '5— _-" "I :1?- “I. _III P .I c —--:'.'.I"I_--'Il".[|'_;. 3, “*3 xx“ fl __ FEET ‘ H ’_ ,1. I'I' "Fr-E: L If; ‘9: fl.» a {TI LH } In} , f |-'- ”Li-II — I'm - ~ *" I J L” h 'h * . -| cw # _. I. - x” 3 a . g ' a I — a, > hgfi {b} What ia the structure Iif'tl'IvEI—mrI'Ipuuan C4H9CI thEE H NMH spectrum is shuwn below. wme a cigar shudure and provide a peak assignment using armws la indicate which ,,--- ~ peak mrrespnnds tI:I each Eat [if pmlnns 'II 9m 131- I2. ._ ' I11:IIL I39. I; \[17 / fll'f'lr": '5' z» ’“ _ F El- Eflflfl JMJ. Fridml. Elm-leaky, Ch Chem. 3A May EDDD. Final Exemlnetlen Page 11 at 1:1 1!}. [1 EFuil'IIS] {at Draw the meet and the least eteble eenfennetlene ef sleet Jed—butyl-rt—ehlereeyelehexene {in eheir ffll'l'l‘l enlr} end uleulete the en uillbn'tlrn eertete nl qu fer the H H lesst stable chair geing te the meet stable ebeir st: EST 0 least stable their meal etehle el'leir Show equefiene used and detailed eeleutefiens e55 Te" fr Tl-—t.e-'s..il .L if: . Anewfl: Kc“: , ' " :«(fiafrlt {b} Shaw lhe structure {mm etereeehemietry} ef the preduct ebteined in the reaellen below: - at Br [CI ' {- -"-"’H5' ‘s_/) a “ files I” H33 EIEI'IHJJHJ. mm. Baltic}. EH Chem. 3A May EDGE]. Final Eminafiun Page 12 m‘ 14 11. [1B Paints] {a} prupuse a synthesis at Hack .r IG=GHFCHR H36 .fflu ,, :6 Fr — 555%“- —J—::‘ .HIEI '- I'll-I] In“; h’ jfl—L? {hhxfl ' ' IfILr r 1.. fl Ifil ' __— —- -—‘ ,w '59,}va E r mm x“ -—— “a “3% "I Jfl _ r."r-.E'.e 5hr .H__r| 'l. ' ... g ‘3' L5- :‘4 ., {H'- Ill,- _ I':I I I] | .J-I".-L_ 'h-__. .I'IIJIILLILIIJI‘ Ill: {fl [/1 rf __—_—I E ..-"' if .I! I5" {1th \\ _EI—|__:I If it'EJ—J M““1""dj-_< I) I' '1'” = - ' ":1 .1} “a" finI firfi._ HJC—C EC—CHa ‘4'“.th .-: ELILEELLL _o—— H CH3 15L“: DEEHTEI JH-J. Flirt-hid. Esmeleyfih Chem. 3A May 2013:], Finst Exeminetien Page 1 3 nf14 t2. [15 Points] Prapese a step by step synthesis of HBEC—CHa—tll H—t: H3 frem ethyne and methane es the Elsiewms at G stems UH haw eH' 5' and - ts- .- '\._'| (film: "' (frets; - I ' ET EEDIKI JJ-LJ. F'l'Eiehel. Bantamflfi. Chem. 3A ltl'tailr Eflflfl. Final Examinatiun Page 14 (31:14 Nate: There are net qu eatiena ta be answered an this page. Mat all at the data provided may he needed Relative reaetittittr at EH banda in radleal ehlerinatian Tertiary: Seeendartr: Plrii'narglr = 5 : 4 : 1 Ft-EHe-Ft‘ 1.2414 ‘tl'alue ef gaa eenetant: Ft = 2.0 eat dag'1 real" :- tea-e1 «at; HeCH 1.4-1} Value at a [lease tar natural logarithm a} e = 2.?1 B R-GHE'ULR' 3-3'3-9 1ll'aiue at aaaeiute zera [HEP-fin} = —E?3“G R-CHECI 3.4-3} RECH Cl 3.9-4.4 RD-GHEG' 535-5 Itraiue nteaen teeteaiei interaettnn feral — H = 0.25 iteel rnnie'1 IInfalue at each 1.3—dlaldat 'tnteraet'raa fer {GHahc - H = 2.5 Real male" tralue nteaelt 1,3-diaxial lnieraetinn tnrel-ta — H =1 tteal rnnie'T 1Itl'allue df butaneegauehe intaraelidn = 1 Real n'ltllliti't Elaaaagg: MGF'EA i5 metarchlruperewhenzaie acid; HUGH ie an arganie pemxidfi: Hm, is the equilibrium aanatant- Partial ariad le ef the etam F‘ 11 . flea ga a- t... E. H I BE 1mm ED Ea mm are 'I' 5!. Ba 1311:: HE ...
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