Spring 2004 test 3

Spring 2004 test 3 - té ti 8 Organic. Chemistry Spring...

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Unformatted text preview: té ti 8 Organic. Chemistry Spring 21104 Test 3 Nmtc_CK€/L{ Dr. was. Scare —— epscanflflflflfi = 9x_5_*1eaes = 129 E}. r‘til' el‘the teIJen-‘ing refer tn the same ctintprinnd escept _ _ _ i 1" r; . A. acetyihenzene methyl pentyi ketene (1‘. acetephenene O a.“ Li”) D. cm] at HUD crn'J E. singlet near3 ppm in the 'H NMR 1. The rneiecitlar fen-nah: fer pentana] is _ _ _ ® case a. ensure. c. case a. cane s. cane2 3. I'ltH It increases in the centptntnd lichen seinhiiity in water___ and its heiiing peint _ _ A. increases it increases D B. increases): decreases _ ll decreases H increases V” C -i. In a tautenter crittilihrittni KL 'Jl its _ is ttSt]Etii}-‘ the deniinant isetner at. wittig the P—D hand is stranger thati the {HS heed ® here the C=D bend is stranger than the lit-C bend C. ene] the {3:0 hend is strenger titan the {'=C‘ bend D. kete the til-=0 hand is 1rccairer than the CrL‘ hend E. cried the {3—D head is weaker than the (“—L‘ bend die i_ iii—ii i3 }1{:L[ I) E) r . , CH3 Cl ii 5? fit C CH”: H. g .. C, C U (Q “13mg “Magi A B C CH3 “if 0 cM CH3 H g CH3 CKCi CH3 n ea3 D. decreases v E. increases fl be cause E) / Cir-1. ii MCI decreases 31 remains censtant “:3? fi. Ketoncs arc V Efl’u‘ *flimk? prone to nucleophilie attack titan aldeltydes because _ at. more the ketone‘s additional alkyl group increases electron density at the carbonyl carbon H. more the oyo all-tyl groups of the ketone sterieally direct the nucleophiic to the carbonyl carbon [7. equally both are carbony compounds ® less the aldehyde's one lcwcr alkyl group decreases electron density at the cgbgrtyl carbon D ii. less the (3:0 bond is weaker than the C=C bond 1: d} ..-— C'. ,_ {H5 is '1. The major product of reacting rliisopropy ltetone with 1.2-etltanet1ithlol Followed by Raney Nickel is _ _ at. hexane B. eyelobexane C. heptane ff D. 2,6-ditnethylheptanc @14-diinethypentane >/ \< V C ... ti.» 5 8. 1iilr'ltieh compound below 1would Ilfl't produce a positive iodofornt test '1' a (3} benzophcnone \ Q B. ctbanal r)? C. isopropyl alcohol My Ha \[t/ D. .t'eeabutyl alcohol E. 2—hexanol W 9. Optically pure aldehydes that are chiral at the alpha carbon can be racentized when exposed to basic aqueous solution because __ A. actually. aldyhydes can not be chiral at the alpha carbonll (13;) an acbiral enolate is Formed C. a chiral enolate is formed I}. there is considerable ring strain E. condensation reactions have a planar carboeation intenncdiatc o H its—ca. [fax ———--I-- 9 fi {ferry H ~ on t‘t-tt/Lkii UK 1 f” NH 1- l N H / no} ts——t:t-1y “NH CH3—L‘-—H L“ 3 [ l (i . o— .— t.t-t_, Iii CHS/ “soc”? I) I ll —-—h-- . 1 / “a UII'ELWT ' 0 ma— 3"" E I: MI; H ‘I 35 he; .x’ {113/ “‘1: U \ EH I T CFL/ HRH I “NEH C'H3’—C'—H C '1 _ Cl—I—CI-i N”3 L CH3/ KCllg D 3 3 A i B c l .+. LEE}. . . . . 0 PIMP—E3: E ' F ['1 CH; 9 U r k w ——-'+ IE‘CHg/ \"H ' CH3 CHE _' l I ll " g c LiHj——C—CH} L. H G) 011/ “RH tux/1x14 I (3111/ “EH; . /C““~ A @ ICHJ D {Ll-I; _ H u: l: T? {HE‘H3L1' /C-\ ——-—T ‘2 13- CH} H {HEM} [HI-I D I. I D U HRH/ill; C H.1_ CH; C1 13:31-15: H3 . H [3H1/ HRH CHJ/ X‘CH; . /C“x A - D - {.H1 H '3 F P] 1H EH Pha EH O 0 - II II ‘n‘ if “M fa Pl1\ /C.._\K {T C (Ii.fo CH1O h H u H 1| CHE/©“HDH CHE/DR” HIE/Fin m CI—13C3CNEL {EH-130+ 1.1. CI-h/ H \n (Ilh [In-Hag O L II {11-11 "EH III I“ a “C” a” T T 'c- ”“ /' ‘9 1 .. CI-L H 0 £1 HEN-fixing Q If. Cl'Ig/ RH ronmtcmp fin NXNl-L ~ NH1 H {rm/L H 0/ \ XH ! 1— I N FH/ RH HM CHr— C'"—'H | a 3 l'i'. "I U I // ECHJOH .3. l-I—~C—f.' ‘—""’ I \ l-ICHg} H H {7H3 rot-t3 CH; 0 "I o It 0/ II o/ I // . |. // J I 1 I H—C-—-C I'liC—i—L\ t-ge—i—T—I-r H—L—tlT—H | \ '- H 0 H o H H 0 CH}, t—tfie/ B ttse’f C @RCH; a H ‘2' {fix/H CHycHwCI-iq D i 0/ _ _ o ergo—t" 3 IL CI-g—t|?——H Ct—lfi—e—oettget[Jet-13 "t LHICHELHi C Ct-tzet-tgetetj ® 1‘}. In the Haeyer—‘filiiger reaeiioo ol'att asymmetrie ltetooe= like MEK. the Eliiij'] group that migrates is determined primarin h}- A. steries — the stttaller allay] group migrates B. steries — the larger allin group tttigrates C. eleett'otties - the least hasie group migrates GD eleett'ooies -- the most hasie group migrates E. Imithcl'; there is a 50:5'3' probability that either alkyl group Iwill migrate. CRAZY FUN HITH RUBBING ALGUHULH Fur quumiuns If} — 15 match 111:: cmupuuncl number with 1111: Emma structure beluw. THC! 5' Base I J l-‘Phj H 3" ———:- ll .r” a” . D 2] MIL] H \ PCL‘r‘CIhCh [‘i1.-"1|3L'J.-’E}]i ' ' 22-———-—r- 23 Hi"); _ 21+}: ~——I- 24 ‘———|- Z: 2} anI-IJD mi ( fie CH. _ 21. E: RCI’CHJ r:MM A H CH3 CHJJI 22. KC [CI/Ts n {r— CH \CHJ l "H — CHE—FC‘—CH3 _ F“ “Ii D 1 PHEFEXPH [1 v D “ H H n ‘ uh __ CH3 CH3 ...
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Spring 2004 test 3 - té ti 8 Organic. Chemistry Spring...

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