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Test_II_3331_E - 1 Nomenclature(16 points 4 points each...

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Unformatted text preview: 1. Nomenclature (16 points, 4 points each) Provide the 1UPAC name for each of the foliowing oom'pognds! g. ”I - 1'.) E_3_. (ignore Q and S '-' ) in this compound) ‘ Cl Hwy [U U fl O v: (3 (D m f (3H3 CngoH W1 l CHzo-H; W i H ..'/ I .omoiete simciuraé cirav-sirag- for ihe fofilowing com r“. _..-~. 'HOQII d . 2. FACTS: {Total Points : 29) Place all answers in the boxes or sgaces provided. \. Placethe following compounds in order of increasing bond dissociation energies (BDE for the bonds indicated with arrows. (izsmailest BDE, Szlargesi BDE) (8 pts.) H H K: KI: 55¢: O- CHCHQCHS OCHZCHQCHE CHQCHCHS . ' l B. Place the following caroanions in order of increasing stability. (l=least stable, Bzmos stable) (8 pics.) ‘_ CH3 CH3 CH3 ~H2C=CH-§H-K5H-CH2CH3 H2C=FHCH2—é—CHQCH3 HEC=CHCH2-C[3H—§H~CH3 e - e» .. -_ 6 0. identity the following pairs as enantiorners, diastereorners, struotiarai iso- identical. (3 pts. each) 3 (D h" 1 or) C T L'l~C . 1‘ fl , fl u H ,HFHECH'B Chi3kJU2a \\CH; I a 6:26 :C\ /C_-: {3:0 I l 9/ CH3 )‘ '“lcc \Pr 5 l ! Fl ‘ . (I ‘5 if, H. :55 -' .1“; H C '_.l I -. a .. “9:"- ‘Cr‘t'i i‘. —~-—----\l~-~F Cit-E l - — ”i1 l ,_ ,‘3 r.__.w,.a ..... Mo. _,._ l‘ 's r ‘75— . l l . .. “75"- «— _.__l"_v.-E ‘ r l..—_.i . 5351 i i ‘ I i if — '——"— — mg on: D. For each pair of reactions‘ predict whether the rate of reaction a is faster, siower or the same. as the rate of reaction b. Write taster, stower or same in the box. 2 ts. eacjr .__.—_ D DMSO ‘1‘) a~CHSCHQCH2—Ci 4 Nat «~—-—-——-———»— CHscHECHg-I + NaCi b' (EH30HQCH2'CI + Na! WCHECHQCHQ‘i + Nae! « ‘ IIll un‘. . 2) 9* fg-ph3)3C—Br <33“? i [Li-1’35 Pi 3:2 b. (CH3D3C‘ET + 'i. ._.__.__..._____,... {CHCJSC'SCHEJ " KB." {1. O a O U , n 4 m ‘ [I \ ,M j p Qe ewtorie p F. U NLF, Q, 95 Cr—ISCWEth-JF * vH‘CL) \ quvhgcu Iz'kjb'ui—i3 {r ‘x F") U C l .—. l5. I \_./'| 1’41.) :3ququ :3 H ’“ :—., "t 4 :~' _ aft“: —:;’i:’—‘~1~r.::+ Q— :::=:::. 3e: E“. ' '7?‘ K".. {x t L“) 3) 0 Reactions (total: 22 points) Please give the product(s) for each of the following reactions in the box provided. Be sure your drawing indicates the reiative orientation of the substituents (Len stereochemistry) in the molecule. The points per question are indicated by each box. - .-- a. H a .- C// NaCN 11 M” {4 pie» C\ ..?DE‘E3\G\, .I f l -' CH3/ CH20H2CI - __.., , H .. “ ' . , -', V-’ " "in . {Notet DMSO : dimethyi suiioxrdei _ . i 1 CH1 ‘ . '-- I ‘_::I 3 . *a-f . ; "r ‘.1 . ' a .. o ..... closozce.3 - * (—- rm. . J '7 . .l - .‘ ”a ; 1 i \ 1 . {No-fie: EMF 2 dimethyifonnarnide} , '- . ., I l . ' . aim“! | . -. , -! ..| . l | 953 i - ' it fir“ . I. ./ :! fix-"w”,VJ Dr '1— SH I . I !. .-: r“ M/X ./ fl”. 'F = al w __.-___Ir.-./ --~../ 6.. :ij I; / l- J' II Ill 1 \ c '. /'1-(Br ethane! CIT) {2 ms) . d. n. u _ — . .. 7. t .x } n E x 8 8w 5.. emf.“ _ RE I . .fi.. 1. x . ./ »l\ ..\ :-"—‘ _ :C.H2 C NBS = N-bromosuccmii'mde) CH3C Hg\ CHac Hz/ (Note: flmg 5‘. MECHANISM PROBLEM : (Totai = 10 points) A. Provide a detaiied mechanism for the production of I and II beiow. Be sure to draw all intermediates and to show all movements of eiectrons with "curved arrows ” (Note tn stereochemistry is not indicated in the products.) (7 pts ) H CH3 CH ’i-i o H30. 53." ‘.IHHCHCH H20 H30 3 H30 3\ OH .. I I cHCHI u . I Br ‘_ OH + CH3 . [cab : + 9.5 I ' H 1/ ~_i/ B. is the orodo cimixiore opI Lioaii}i active? Cici; “Cr _- or NO. (I pi.) .A In any r I .-I-_. '--e '1... I. : I I -.I.I m MIN-2.2m -.-i. 3s iiII- io-“irrI. Iii-I. .I--~. or c: I-niIIc Io. “Ii 1 rosi I. i . i irI-I-e-.s.-c-r-.-. :eienf'o-i or IIIceI.i..»:e.Ii-I.~I JVIJ of I. i'3 or; ii '“Lii’iii” i oi the c a- ..itIo: i raw/1' -I_. ' 2"? III i .‘I, ""2 '_.I(Ill..":...l. l-"""'-'_'.". _Ill. “NI-1;] II'._.‘.;..I.-.I,I..II._I ”SI-I'll: ." ,-i liH, nod-i iLJ’I,J.ij.'U-I.I'ii '.,:.- liI'I_,- i._.;_,tl ._.-I.,-.. -‘.lL_.L i ' ...
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