Problem 1 AL-4> 224. CH4 “CHa St: CH3-CHU-C g CH3-CH1-c —CH3 Ort =A. | 533 3.91 A= 0,000L| 4 r ——— 7 4000 3000 2000 1600 1200 00 (0.0 V (om) 100) 7 Mass Spectrum | 9 sf. sok —_ 2 i Ich3} g i: i real . idea 1.0 4 ore —- ss3ng0m 20 1emeet soWvent ethanol t Catto | sh 40 80 120 160 200 240 280 200-250 300 350 mile (nm) ; i 1 T T T T T T T T T "3C NMR Spectrum (60.0 Miz, CDC, solution) Scanned with CamScannerProblem 2 ° Cy -CHa- 04 Mt squU-us = 23 © (Hy Che ge S90 cth-cla- © Scanned with CamScannerProblem 3 WB: O= C —CHy 8i-ur ous 2 O-CHr CH cH -CH2 —0-C - Che om 2 a 3.3540 az 912.2 0,000 cm" i 1540 2000 1600 1200 +~«©~«600 «(Of Vv (cm) 100] - Mass Spectum | 95, BOF sok g W spect 3 2 1.0 vent: ethanol 40Fe Mes 88 154mg! Ome 20] fathengh 1.00 cm aH, a “aHgO2 ae : 4060 120 160 200 240 280 200 25030080 m/e Alam) EAE A A ee ee ne ne T a "3 NMR Spectrum (600 MHz, CDCI, solution) Scanned with CamScannerProblem 4 wor Mass Spectrum ot, 7 obs absorption above 220 9m : 2 T <4 nar a ae ee NC NWR Spectrum (ise ues Com, eueen) ed _— 200 160 120 80 40 0 5ippm) “HNMR Specrum op nm. £00, tater) L 10 &{o0m) 93 Scanned with CamScannerScanned with CamScanner IRs a rekbehProblem 6 ony - Ue c - erty % Mtoe ° Mags ey 2 Oe as + Geers Anas 289.M (loa ige 1-4) seteet: manana! I °C NMR Spectrum (100 we, CDC, sebiion) DEPT crud crt cnt {on docouples sovent t ! ——4 aa itis 1 200 160 120 80 40 0 8 (ppm) NMR Spectrum ste, CI, soon) ms 1 Se ee 1 9 8 7 6 5 4 3 2 1 0 5 (ppm) 95 Scanned with CamScannerDATA_L = C42-Cay Isimetas No significant UV absorption above 220 nm STRuUKTUR NBC ~Cth~ Ct, -CEV Scanned with CamScanner 1Wf, Spectrum No significant UV absorption above 220 nm Me atta (1%) 40 80 120 160 200 240 280 Scanned with CamScanner3458 Vv (om?) Mass Spectrum % of base peak Mt 118 (61%) Colt1402 13 NMR Spectrum (100.0 MHz, CDCI, solution) Problem 9 Hy “Hs S92 W-¢-¢ -oW : too Hl amis Cas CH PR Specan e Solution) WO-toy yp - 4000 3000 2000 1600-1200 200 3 > Uy No significant UV absorption above 220 nm DEPT ci} cist cHt proton decoupled ‘solvent —l SY ae Pe es ree ere ae eee 200 160 120 80 40 1H NMR Spectrum (200 Miz, CDC!, solution) Exchanges with D20 ST 0 8(ppm) TMS: Scanned with CamScannerProblem 410 uh aa NE ev te OP a ee Oe Ge 8 9% 7 3 Scanned with CamScanner¢ | ore FE or os | No significant Uv “ops absorption above 20m oor f i E GgHgO 280 mie [ecnumseem ee 13¢ NMR Spectum | (100.0 MHz, CDCI, solaton) Scanned with CamScanner7 Problem 12 nz: i (eso p) cH3 - Ce CHA CHa 19: 1 ee +1. 1 1 1 00 2000 1600 «+1200 ~=—~«800 Kea-bc V (cm') Oe 2q.oi5 + 50 a: ot Mass Spectrum rd Mt"= 156 >0,001%4 Uv spectrum cus! ar 5.00 mg /10 mis contains a halogen TF path length ; 0.50 «em solvent : cyclohexane 80 120 160 200 240 260 m/e = T T T T T T T 1 Scanned with CamScanner| al ~ > el Frobtem 12, / ia | De: SPrie from Ue: CLH — Scanned with CamScannerROA Seite 14 i | f it k mt PLIES “roa Ba we 60-21 Li i te 2) Go-4f6 2 Io, Ro signifcart UV so1orotan above 770 nm Cy — CH-CHs w oH anid jp hg hele ag he el 1 | 200 160 120 80 40 © 8 (ppm) *H NMR Spectrum (200 N42, COC woston} expansions —— ee CS — tus am a 13 em scenes wn0yo SY A 1 i 10 9 8 7 6 5 4 3 2 1 0 (opm) 103 Scanned with CamScannerCls- Ce -CHy -Br 7 Problem 15 Me at Mtg age chs of CHS” CHa -CHs 3 Mr - 43+ 3g br No siieart sors sbove 220 {3G NMR Sperm (goontn, 022 pert oni ont of Scanned with CamScannerProblem™6 CB chs -Cla-dh- cB ule ng $4 = fl -H-el No significant UV absorption above 220 nm Scanned with CamScannerOe CML CH = CH - HBO MieID. 299 Ge mt 129-99 Oe" Ns hrs Go He Be As cue- ai - Ue ‘Mass Spectrum yannas . No significant UV Misaoataay absorption above 220 nm 120 180-200 mle r TT | 136 RMR Spectr | —— (800.0 Miz, COC, sehtton) DEPT Che} crt crf 0 (ppm) Scanned with CamScannerh _ Problem 18 Ane Cay CA 4 Ut at Ut-u IR Spectrum iguid firm) - 4000 3000 2000/1600 1200-00 V (eni") ty Oty Ca CH | 100] Mass Spectrum oH Of § No significant UV of 3 Me absorption above 220 nm ae a 156/158/160 to7n09 40 80 120 160 200. 240 280 mle T —T T T T T "36 NMR Snactnum Scanned with CamScannerProblem 19 68 = CH.- CH, - cur - CEN mt- 68 279 — Br Gr -CHe-CHa- CHa — Mass Spectrum No significant UV absorption above 220 nm 40 80 120 160 200 240 280 Scanned with CamScannerPRbien a9. = So det “Me ays cwy. chy MY TAY sos -cH no, mA 18 . a: CH. Loe - CH, Bo, Ser ukektuc, CHa cH - CH, : ao, Scanned with CamScannerProblem 21 w Clig—CH2 -O- C~ CHa NI IR Spectrum emcee At 108 209800 306 (Ha -0 cz0 70 Scanned with CamScanneraay ap GHe Oo 9g = UHy- Ut UM, Ua g3~ (My-te -Ub 2 Ut, Ee [od * Clo — (Hy ei —lo- G cL Scanned with CamScannerProblem 23 Ot. ch=c# x Nx cA on Nen- cH? (8-91 214 + O-4 Uv Spectrum Year 243.0 (lop gf 1.9) Yrmas 248 0M Gog 6 21) * Amer 242 nm flog ot 2.2) Remar 258 nm flogigt 23) Damar 264 FM flogygt 2.1) Nee: 2080 (og,3t 19) soe eat! (900 tte, COI, so'tord DEPT Cop On! cnt 200 160 120 80 40 0 8(ppm) HNMR Specrum (coe COO, slsond — Exchanges wih 0,0 | . — r 78) 7472 pen Scanned with CamScanner keesimpdn = oneRe Problem 24 f- ae he et, a ‘cw — CHL hi one (70-91 =.99 : Or or OY = to Aeab-c 0d 2.010 -Mi qa: od pt 3000 2000 1600 «= 1200 800 0.0) V (cm) ai Mass Spectrum | 9.5 ot OU 20,0436 UV spectum ew! 1.0) 0.917 mg / 10 mis path length : 0.20 em Mt ‘solvent : hexane 170172 C7H7Br 60 120 160 200 240 260 200 250 300 350 Scanned with CamScanner“Mp Problem 25 3\ :ch ach / ‘ cz: cH i Seu -Cc 1600 1200 800 mt_oy 2b => can - ) Mass Spectrum Scanned with CamScannerCA-CH-CH-CH-cH-cH-cH NH ry, fw i ~ ‘i 3G NMR Spectrum _reten decoupled 200 160 120 (900 Mis, COC! soho) 1 ‘ =——— | DEPT cont cout ont sh a oom | | nn et + 80 Problem 26 Mt = 107 Mt Ay = to = tha A\ =» CH -CH-CH-Cu-ctk- CH-CH UV Spectrum Anas 258 0 fone 22) Anes 2541 (Gg 2.3) seen 40 0 Bien) Scanned with CamScannerPROBLEM 27 M* 2 \22 me) 230 -¥ CHa -0 Mt gi = 317 CH. OF OV —y CH -CH-CH- CH- CH -C -Ctl 2 2 > CH-cH-CH “OO OCH, SAUUKAIUE rae Scanned with CamScannerAbsortuitas = abs Cl,-CU2-C-¢ - nl ° . < i 1H Problem 28 | \ ~ " A f) {PO =L.gir . \ i loys y ij SONS 2 OU g/t | Yi | Dore 20,0018 4} Scanned with CamScannerc Cig = CH, ~chy - 0-6 ° @ ~ Cty Problem 29 Pleo: 43 | [fems AS me ago | ole = labsertigitas = Abs bec AR Spectum #06 = OcoIs LY (iui fn) C0 (Karbon) 05) x780 ew 1 1 1 . . 1 4000 3000 2000 16001200 00 (0.0f" 4 V (em?) j ano) les 43> cw,-E Mass Spectum | 9. j 80F Miya 231-6 i { cok = | ‘1 cts Ghee ; fe | | sof solvent: yeichoxane 40Fs Me 740mg toms 1 7 | a path inngih 0.80 em | CoHio° a 150 1 x 40. 60 120 160 200 240 260 20028030080 m/e Alam) Scanned with CamScannerProblem 30 uve 0 WO 5 4.011087 a7 Lo OFF 13¢ NMR Soeur (ooweces su) \ % —-. \ etna nd \ Scanned with CamScannerProblem 31 7 3 na Gy CH I 1 “ 1 IRS (Ts @ 3000 2000 1600 4200 ‘800 | t V (om) a? 4000 i. 109 5. My- Cy o¢ oof s 2 ty CH eg Tot ot: ape Hy- 0-0 - WOE a2 an cH cH Z ot a ne ee 13C NMR Spectrum 136 NM. (80.0 Mite, COC, woktn) (200 mu DEPT chit cH} CHE Di sehen Pro {rhea aed L eet eee if 1 200 160 120 80 40 0 &(ppm) 'H_NMR Spectrum ‘HNMR (200 Nt, COC, sohtin) 200 Kei, 0 & (ppm) 20 Scanned with CamScanner‘ Problem 32 ” MQ -77 = 7) we f° aig c¢ -cH x " aa i ° cH cH | Vseeaue + ns Crew CHa -cH ec " Mass Specttum| Uy Spectrum Yemax 241M (lO9q& 4.1) solvent : methanat 40. 80 «120 160 200 240 280 m/e Scanned with CamScannerProblem 33 ig: CHa’ 2 (B43 Use Cy Gta t [53 sone 2 ¢ ea CHCl y aoe = CHecHa A rCHe f 1 a 43 Cig GHP -O-€ Mass Spectrum 2° . oe CHy-Ge He _(ycd -C-E-tHe~ CH 60] No significant UV absorption above 220 nm 40] 20 Mt 158<1% CoHy403 qo. 80 120 «160 200 240-280 m/e 130 NMR Spectrum | Scanned with CamScannerProblem 34 Mt ty Woe On, seu, 5 ond cll . ° mr &. ¥ " . Ws 29 = c =H tS Bs tn 200 uu * C2 -CUy - oO Strvtiuy ; Scanned with CamScannerProblem 25 ° $059 CH-cH~ cc -cH ce ~ Hf pe Ves cH -ct oH tH ~e ° aw 5 wy a a dea ax on Yen 25809 (ogy 42) ewe 3000 tgygt 28) Dat 38.09 fog 22) Scanned with CamScanner“mn «. Problem 36 - * - mf c Werome aawt GC MLO = cH een Se Ot " on-cd 1600 1200 800 0.0 As abe (em?) a a0 ED v ‘Mass Spectrum 20,026q8 ow! abeorbance, wsmean | 185.3 mg/ 100 mis puoi: O2 em solvent: ethano! Me 182 10 160 200 240 230 200 250, 300 350 Je 2.(am) = Resches nto wo signals a higher kt + Resolves into ‘wo signals at higher felt \ scien Scanned with CamScannerProblem 37 al: ne x loo- at =I RK loe + Com I Wray Ou Tn. T re ae T te Scanned with CamScannerProblem 38 a4 > Gia Ca = Cle \‘S * a GR —> W - cts - Cth - OH We ‘Mass Spectum ile -CHs = Ww No significant UV absorption above 220 nm yu dae 44 Gan) @ : ee CeHieN2 go 120 160 200 240 260 m/e 160 120 80 40 0 (ppm) Scanned with CamScannerProblem 39 Pre: 104.1 mo Crore 2 16410 O/t Mysorttfitos » ABS ven 2°04 3 boos ed YL ° ga 4g eCuy-6 ° rte gg WA Hg meek a + cu. 7 UV spectrum Elpchenthystrso 104.1 mg 110 mis pathlength : 0.2 em 99 ye CgHyoO2 solvent ethanol Scanned with CamScannerProblem 40 ms 18 29. CHs- CHa 4s + O- CH2-CHs 2 MT. 45 > 43 — CHs-CHa-O-¢ Struxtue ° " CH3-CH2-0-C-O- CHa- CHy No significant UV absorption above 220 nm Scanned with CamScannerProblem 41 wt = Bo ag 2 cHa-CH? : IR Spectrum FF ow ue GE a " OW - 6-0 - 43 ae -b-0- Hg. iets yg 14000 '3000 28 em fe “a0 Gee at -ag ste! og © or fore cg 0-6 eH oof wasssoemn | att ga = qaactts yerir o- a No significant UV 5 absorption above 220 nm “ evetuc a a 2 re » Getto | cH ge cthr~ O- Em e = CHa i ite ; mie 13¢ NMR Spectrum (800 Mie, CDS, setidon) (ook, COC, soon) sotont proton docoupiod oy yg dt abe a ey 200 160 720 2 77} La 1H NMR Spectrum Scanned with CamScanner——— ‘\ Problem 42 L=0 = 56 1768 1746 pacha 2y:16— C-0 3000 2000 1600 1200 800 Vv (cm) ' Mass Spectrum ee | =a & = O-CMg-¢ : cHg-CHa 0-6 Geu _ 4 0 2g a an A as 146 (<1%) Celt 10 Os 3 oe a4 p40 200 160 700 a il Scanned with CamScannerOo 48. Cc ow 42 = Gtz-c-0 Oc = Oe He rots qs e WC *Crlr-e. ¢ ~ ena ale CMS o & 6 @ Scanned with CamScannerCie CHE = O- © - C- G-O- Cy 2 . spectrum (teu fer) ir) 3000 2000, 1600——*1200 800 V (oni!) Mass Spectrum Me ub 1% 40-80 120« 160-200 240280 mie Problem 44 ait Ce eat CHz+ © Ba Pes oO |G 3 oO 59> cwy-0-& Ws- gq 2 nee ate Oe Ws 692 $6 9 G-0-0-© 3 ctr -Urle = 67 89-5972 Ga Tih an / c=0 No significant UV absorption above 220 nm NMR Spectrum 90 Miz, COC! solution) * DEPT cit crt cut i ., 0 8(ppm) Scanned with CamScanner °° ° ‘ ty Oh - 0-€- ~~~ ts Problem 45 w= 146 ta - $9.2 S99 CH- 0 dye eua-§ fF Oy- Oh Oh ° ° 20 BPe Ues- (rh= O- C= CH 4000 3000 2000, 16001200800 Vv (em') 0 Mass Spectrum 6 40) No significant UV : a) ‘absorption above 220 nm 48 (61%) ao Mitta 148 (61%) ao. 60 120 «160 200 240 280 m/e Sot Sao ea ¥ r 3c NMR Spectrum {enomcOcl wtton) CH 200 160 120 80 40 0 &(opm) ‘H NMR Spactum (300 mite, COCK, sokton) _ | mus 0 i I | Scanned with CamScannerProblem 46 Mt = 146 MSs CHG c- GH-cHy ay \ 1 "46-155 3) on oH BY = orl -CH2 JR Spectrum: (igus en) wn ba, sees) , 4000 ‘3000 200016001200 ‘800 \4oroun- 7 2 (emit) 4bz0H cH, cue hie tig oH on 109] @ Mass Spectrum a0k = 60} : No significant UV 116 40FS ra absorption above 220 nm ’ ae 20 Ad a CelioOg 40 80 120 160 200 “240 280 mie La ne a Scanned with CamScannerProblem 47 Mt 21446 BY-S9g =28 — Fb 1 7» O-¢ \ 1200 800 a — oO re P § Mass Spectrum I~ c z Sst ig No significant UV absorption above 220 nm Scanned with CamScannerProblem 48 ° \ ww OV = CHg-CH,-CH ctl, -0-¢ Mtl 101235 CHW, -0-!! Stekoes ° = ‘ eet Cyc tn Crea C-OmE- Scanned with CamScannerProblem 49 G72 CHz- chi -' \ MP6 7 WT ety te paFo-y . et CHg CHa CHa Cy B~ C0 - 6 Oe Hy ) 2000 1 1600 1200 800 Vv (cm') Mass Spectrum Kabat __ oe Scanned with CamScanner1755 IL=O 1820 ptt gt 2000 1600 1200 800 V (em") Mass Spectrum Problem 50 © 71 2CH3-cH,-cH,-¢ + ‘ MH 2 87> CHa -cla-cHt, — Co Po ° Cty - Oa - CH, 6 OE = CH, Cre CH ee ¥ No significant UV Scanned with CamScanner