Final_H - CHEM 2332 ~ Find EXAM CGH) A' Nomenclature? TOtai...

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Unformatted text preview: CHEM 2332 ~ Find EXAM CGH) A' Nomenclature? TOtai = 12 pointa 4 points each ‘ " ('4' - GiV-é-an. fgf each of 1h? ‘ Z ' 9.- hgfilVb‘Nf * [flfl’lflfizj J — 5 “O L-fen *3 "ENE" 3. ngwfiw (aw-ammo” N‘pmpwhgmmm O ' ' . wit-a. B. Rgactiqng: Tara! {Lgpginza 8 paint-S each ; .-7 , _ Pleaséfprfiyide-theSt H ggi‘materia'l, Majar'pradUCt-qr necessary reagents in the .answgrbox- Bje' guneyou-r drawing 9indiaeresfitereecfhem'istry-rif applicable; Pafiial credif’isi'awaard ed-omy‘ {When iifit‘ewnédiate 3-prb-duc‘ts are sh'oWn 1béioW1H~éfiééCflgm . - ' ' CH3 I. I . COQCHS + ' .1..-.Heait__ ———-———~—-——-——e> . 2.'l_-iiA-Jll*i4i-(3<S) ON 3.. H20 . CH3 @ H Nags / 1142.5'0‘; @ am Fear-5 451?? 0 CH3 1. MCPBA 3. 2. CHaCHgo ' Na + enaflf 3. CHSI 4. NaCN /H+ I H30+ I heat 0 (if Q U 9’3 l . 9 I (it .9“ /L\F_HC H2 (3) 1 v, -_,f h H. - ‘ 1 ED —“’ 1, l‘flfx‘" _—a—v 1“" OH H K .\ t ‘fi ’ ' '_. E - LR"; ( LN-v’JH!’ .~ "L‘ 1 L J I L 2 J D UL .~. / If; ' “~— {51 ’ a {SCHJ P 0(Hgfi’ Hi. ffifififiufi C. Mechanism: (“18 points) Provide reasonable 'mscha'rflsmS'fm the mac-Lion balow. Us: curved mews to indicate “electron flow". Show-2111 intermediates '_and 31:1 formal --c«harges.h_ ‘thcrc. is mogexhan one resonance structure,'you must Show. the-"best" (1.3., lewest energy) structure; ' ' ‘ - NaO Et 1.1KMn‘O4I "OH _/ heat. ' 2. H+- ‘ 3. 'ZSOCI xs 4. NHa (XS) :5. Bra] *‘OH/ H2065) w to H413 - “ ' “ f' -*-=' —=» . o 0131;, :2 0H. m " ‘ '0 ”‘-‘ r} ‘" Y‘- W . - ‘ M1415 _ @3qu a CH “‘3 "NEH-i . . .. v’, hI-I‘ .~ ' 1. CHSGHZO - $213+ 1’ EtOH OCH 0 2! H30+ " 3 II -I [I CH3OHe-CaCaCHéCHz—C-CHS , 4:169 ‘3‘" fl” - o g? _ __ = 1%.. ' ' . Q}15¢H;6_ C— L. comm; war/Hie c— C—ocfichg l . .. o 41,, H - Hzctfa .4 CfificfizCo—C*OCHZCfi3 i 03'} D. Synthesis: (18 points) , Synthesi-‘ze the molecule .bgiew usin'g'r-my Of the, $1.10“:ng inneragentszr alkanest aLkenes, aflcynes,‘ or alcohols-of two 3carfbp_n_s_ Igor lessglbenzene, any moi-game reagents, any'oxidiz'ing‘ 0r reducimg agents, and any peroxyacz'ds. " ' ' ‘ . - . . _‘ l n wacCHzCHzfl‘il C- 061 -——;~ T'H’Ten H90? E \I 1' N’ET + E? if r ’ C =cH-c-a ‘ cHacscHz “2, T Tmmmw 3* “51:71 Th ‘uaw: fi/kjfl E Ear ' C-Hsv‘dr? * H N ' , v5. . ‘ 3 2 uHfiréfi b JE-i T Brzjaéfim a} m at T901 \ mun-«:3, a“; { CH'2: 3‘: HZC’HZQH DH f ' a: T i 2"» t o u l Cri'LBC'HEI‘f‘H /Al(_.f3 " + ‘ v. (“HT-CH-H'Br + can ‘ ago—H flhflqfir 3 3 / H J faxk $mmw g;fi&fl{ b // (a I ‘ fl , . . C5“ CHZCMQ H. W// CHaflfar‘ (mflki \ 3 - NLDLIIIIE'EH‘f 2 If HEW I (L? 1’ Ja m! CH CHE CH? of H H 4.» .—»_ -,_ ._ I (HEC’NflflfigHQ L Cva H I T ICHgfi'F’j It? E. Spectroscopy: (12 Points) _ A campognd with Lbs fo-finula C3 :cxhibi‘ts. the IR, 1H ..ami _pm£_®n—.deo.0upled 13C NMR spectra shoWn on 'tha fdllowifig 'pilge. Please identify this compound-and draw the ' structure in the, box. provided beiow. c 03/7 “pa:ng 0+3; 3! IMI‘IH‘IMZE MP moi-11203 8.5 8J1 LE 7.0 6.2% '4. Proton NHR 150 .' 140 120 190 an 50 4o 20 PPM‘ 0 Carbon 1'3 NHFI ‘ D TABLE 13.2 Characteristic infrared absorptions Cir-groups ' . FREQUENCY GROUP ' WGE'Igm'”) . WSW“ A, Alk-yl ' C—H (scratching) _ 2353—2962. (m—s) H lisqprppyl. —CH(CH3}_1 _ 1389—1385 (S) and 1365—1370 (5) .ren-Eutyl. -C(CH3‘-)3 i 1385—1395 (m) ' ' and ~ 1365 ‘ (5) 30-10-3095 (m) 1620—11580 ‘ (iii) 2985—21360 ‘ '(s) and 39055920 ‘ . m _ - 8304960 (51 , ‘-675—730 (5') 9-60-1975 (5) C- Alkgmyl Ec—r-l (ml-ailing) ‘ ~ 3309 (s) CEC (stretching) ' 2100 ~2260 ‘ (v) D. ‘Mhmafic Ar—H (strctchiglg) ~ 3030 (v) Arammic substitution type '(C—I—I um—of-piane headings) Monosubsfltuled 690 -.7 10 (very s) and “ISO-«770 (my 5) a Disubstituted 735—770 (5) m Disnbsticured 630—725 (5) . and 750—810 (very s) p Disubstimted 800—840 (very s) E. Alcohols, Phenols, and Carboxylic . Acids 0—H (stretching) Alcohols, phenols (dilute solutions) 3590—3650 (sharp, v) Alcohols, phenols (hydrogen-bonded) BRIEFS-5:50 (brand. 5) Carboxylic acids (hydrogen bonded? 2500—3000 (broad. v) F. Aldehydes. Ketones, Esters, and Carhoxylic Acids CWD (switching) 1630—1786 (s) Aldehydes ' 1690—1740 (5) Returns 1680— 1750 (s) Esmrs 1735—1750 (5) Carboxylic acids 1710—1780 (5) AJlech 1630—1690 [5) G. Amines N—H 3300—3500 (m) H. Nitrflfi CEN 2220—2250 (m) ° Abbrcviau’ons: s = strong. in = medium. w = wcak. v = variable. — = approximalclv. A. Nomenclature: (15 points, .5 points each) Please: provide an acceptabl'E-nameforEach jof'fh'e-zfoliewing compounds. Bagsure'ie note stereochemiStry wherersappmpriate. fu 99ch H3 3. /w« l E: ...
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This note was uploaded on 01/05/2012 for the course CHEM 3321 taught by Professor Bean during the Spring '11 term at American Jewish University.

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Final_H - CHEM 2332 ~ Find EXAM CGH) A' Nomenclature? TOtai...

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