TH nye Problem 1 IR Spectrum ‘eu i) i8 1 1 1 +4000 3000 2000 1600=«=«1200=S«800-«.0f™ V (om") = 100] Mass pean | stg wok 5 3 at | i we | Mf 10 = 233mg 20} 9 toon enc sehen ean 1 4He0 | ek 4060 120° «160 © 200 240 260 200-250 «300350 mle A(om) TE 13 NMR Spectrum (600 mi, CDC, stator) setent ‘proton coupled : secon decouped (a 200 160 120 80 40 (0 5(ppm) *H NMR Spectrum - (200 Mi, C00, sain) : ws Ao 1 4 1 1 1 1 L 1 4 4. 10 9 8 7 6 5 4 3 2 a & (ppm) 90aw Problem 2 200.9500 IR Spectrum hai hr) ins L 1 1 . 4000 3000 2000 1600 ~«41200+~«=«800 V (eni") La Mass Spectrum wok < a 60F g owe No significant UV «fe 7 absorption above 220 nm sr = 20 C3HgO. 4080 «120° «160 200 240 280 mie 5 a a *9¢ NMR Spectum (6000 Me, CDCI, sokten) DEPT ct} chst cHt proton decoupled scivnt a a a een aan 200 160 120 80 40 0 Bi(ppm) SH NMR Spectrum (@uv me. COC! sotton) exchanges "wih 020, ' J Se eee eee one ws 1 L 1 1 1 1 1 1 1 1 1 ! 10 9 8 7 6 5 4 3 2 1(qui fm) at Sun Problem 3 rm 120 1 L L . . . 4000 ‘3000 2000 1600 ~~ 1200=«=«BODSC«O : Vv (om) [ 100] Je Mass Spectum | gs sof x i & ok Yo uvspecrum 10 5 salvet: hana ors MY= 88 18.41mg/ 10m a df amet | CoH aHeO2 | 4060 120+ «160+ 200° «240 280 200 25030080 mie (om) TT '3C NMR Spectrum (200 te, COC!, statin) DEPT CH} CH} cut proton decoupled seven am a am eee ee eee eee eee 200 160 120 80 40 0 8(ppm) "HNMR Spectrum (200 ts, CDC, calation us + 1 1 1 1 4 1 1 1 1 1 L 10 7 2 9 9 8 6 5 4 3 5(oon) 92—- Problem 4 1R Spectrum me peal 4000 3000 2000 1600 1200 800 V (em) 100} Mass Spectrum 9 s? pec BOF s cok § No signifcant UV woke Meas absorption above 220 nm 3 20} C4HgO2 480 120" 160°” 200-240 200 ce ‘3 NMR Spectrum (tose wes, coc, etter) DEPT cH. cest CHE pron decrnl sent 1 1 1 1 1 a 200 160 120 80 40 0 8(ppm) ‘H NMR Spectrum eon cite ounce \ 10 9 8 7 6 5 4 3 2 1 oO 5 (ppm) 93IR Spectrum (iui im Problem 5 4000 3000 ‘2000 1600 «—«1200~=«=—«800 V (en) 100] Mass Spectrum sok = ar 107/109 & sot No significant UV we 7 absorption above 220 nm 20) ae 196/188/190 _ CoHaBre 4060 120° «160 200° «240 280 mie TI 18 NMR Spectrum. (600 wiz, COC, solaion proton coupled proton decoupled Sf . rio oe eee peer 200 160 120 80 40 0 8(ppm) 1HLNMR Spectrum (200 is, COC, soto) mus ae L 1 1 1 1 L 1 1 ! (eee 10 9 8 7 6 5 4 3 2 1 0 (ppm) 94ay F y \ f IR Spectrum Problem 6 esis we | L L ft ‘4000 ‘3000 2000 1600~—~+1200°~—~=~=«8O0 V (omi") +100] Mass Spectrum UV Spectrum cok « : eo a Amax 289 nM (logy 1.4) ‘ole seer; ar 3 oe e Mr = 06 20 CHO, 40 80)«(120«160 «200 240280 mie 7 1 —— Teal Tt 19¢ NMR Spectrum (00 Mz, COC, soon) DEPT cit cHst CHE proton decoupled salvent 1 200 160 120 80 40 0 d(ppm) “HNMR Spectrum {@00 Mis, COC, solwon) THs fe 10 9 8 7 6 5 4 3 2 1 0 5 (ppm) 95Problem 7 IR Spectrum zea (KB disc) 40003000 "2000, 16001200600 V (eri*) 109 Mass Spectrum ok 7 sok § No significant UV aks) | Mt=00 absorption above 220 nm 2 20 CyHaNo wo 80 120 160 a0 240 260 mie a 8 NMR Spectrum (00042 CBC, soon) — DEPT cist crt cut Fron ecole a fa orf nh ne Ae not 200 160 120 80 40 0 Steen) "H nr Spectum (toons cl non) Hs 1 ~ 0 wo 9 8 7 6 5 4 38 2 1 40, 96IR Spectrum Cia fm) 4000 3000 2000 1600«—«1200-=— «800 V (emi?) 109] ‘Mass Spectrum eof = a oot g 40k 2 20] Cotta 240280 Problem 8 No significant UV absorption above 220 nm *3¢ NMR Spectum (600 Mitz, CDCI, soko) DEPT cH} cHst cHt proton decounted sohent 4 | 200 160 120 80 40 0 8(ppm) ‘1H NMR Spectrum (200 re, CDC coston ™s L i 1 Hi i ni ni n 1 i H 10 9 8 7 6 5 4 0 3 (ppm) 97Problem 9 IR Spectrum (Cis ster) 4000 ‘3000 2000, 1600 1200 ~—~—~800 V (om) 100) Mass Spectrum ° BOF § cof g No significant UV i 40k absorption above 220 nm * Mr =179 (1%) 20} 103 add a CoH4On 4060 120+ 160 + 200+ +240 ~~ 280 mie T T T T T T T *8¢ NMR Spectrum (100.0 wiz, i, saluton) DEPT cha} crit crt proton decoupled ty n 1 L L L L 1 1 1 L L 200 160 120 80 40 0 8(ppm) "HNMR Spectrum (Poot, CPI, saute) Exchanges with 20 ms 0 8 (pm) 98Problem 10 IR Spectrum {KBr disc) 1683 4000-3000 2000, 1600 ~-¥200"~—~800 V (oni?) 100} 36 Mass Spectrum aks Me =ste cok § No significant UV mia absorption above 220 nm : 20 CeHgQp 4060 120~160~ 200240280 mie EASELS a '3C NMR Spectrum (100.0 mie, Cb6% ation) DEPT cH} cH} cHt pecan decoupled nent a 200 160 120 80 40 0 8(ppm) 4H NMR Spectrum (wont, Cn, satan) ws L 10 9 8 7 6 5 4 2 1 oO 5 (ppm) 99Problem 11 _ {ft IR Spectrum (igi in) 4000 3000 2000 1600 «—«1200~=«—«800 ‘Vv (cm") 100 ‘Mass Spectrum: 20} att Nee Msg 7 wht absorpion above 220 nm = 20} CsHg0 4080 «120°«160+«200:«240 280 mie Aan SEL AL RL 13 NMR Spectrum (10 0M, CDC, soliton) DEPT cit} crt cHt roan decouples sohert 1 {| fee eee eee ee ee ee ee 200 160 120 80 40 0 8 (ppm) femeenat comin ae 72 Pew ne ae 1 1 \ 1 1 \ 1 1 L \ 1 10 9 8 iw 6 5 4 3 0 8 (ppm) 100Problem 12 4000 3000 2000 1600~=«1200°=«=S« 000 V (em") 100} Mass Spectrum | 9.5 oy Meese g 60] ; UV spectrum 3 ath ang 0 5 om : conaine a haogen tor eysohnane 20 15) 40 80 120° 160 200 240.280 200 250, 300 350 mie A(nm) 1 TT 13¢ NMR Spectrum oe {600 Wis, CDC!,zokiton) thatomple sohent proton couples | on tf bw 1 fe eee ee epee 200 160 120 80 40 0 8(ppm) 1H NMR Spectrum (evo me, Cou souton) 1 1 1 1 1 1 \ 1 1 1 1009 8 7 6 5 4 3 2 1 0 8 (ppm)Problem 13 yr i IR Spectrum iu) 1 \ 4000 "3000 30001001200" 600 V (em') ‘100 Jes Mass Spectrum ook = a cok s No significant Uv wake . absorption above 220 nm 2 Me 20 seroore2 CoHCl 4080 120+ «160 200 240 260 mie TT 13C NMR Spectrum (600 tz CDCI ston) pron coled Proton decoupled seven 1 1 aan 1 200 160 420 80 40 0 5(ppm) 1H NMR Spectrum (200M, CDCI, soko) expansions, 80 58 pom 22 20 ppm sus 1 4 1 1 1 1 1 1 1 1 14 10 9 8 7 6 5 4 3 2 90 3 (ppm) 102IR Spectrum Aqui i) Problem 14 4000 ‘3000 000, 1600~=«1200+~=«=«BO0 V (om) 100] as Mass Spectrum SF x sok g No significant UV as absorption above 220 nm 7 gg MTs C3H,0 4080 «120 «160 «200 240 «260, mie a *8¢ NMR Spectum (600 we, COC! soliton) ‘oten coupled J sotvent proton decoupled ee eee eee feet aaa 200 160 120 80 40 0 8 (ppm) *H NMR Spectrum (200 Miz, COC, sokton) expansions os eer oer rie 15 To ppm exchanges a wih O20 Sf 7 i 1 n 1 1 i n i L 10 9 8 7 6 5 4 2 1 0 8 (ppm) 103Problem 15 IR Spectrum tM ‘ii fn) “5000 76001200800 V (env!) 109 o Mass Spectrum eof = a oor g No significant UV whe re absorption above 220 nm 7 sie C3H,Br 40 80 120 160 200 240 © 280 mie T T T T T T 7 T T T T T *C NMR Spectrum (600 Miz, COC! solution) DEPT CHa} cHst cHt Proton decoupled 1 L L L Hi L 1 L 1 1 fi 200 160 120 80 40 0 8 (ppm) ‘HNMR Spectrum (200 Miz, CDCI, suksion) expansions 104IR Spectrum ‘i fn Problem 16 «0 L 1 1. . 4000 ‘3000 2000, 1600~«—«1200~=~—«800 V (em) 100) s Mass Spectrum oof oof § No significant UV wet racer absorption above 220 nm z ~ 20} e CaHeCle 4080 120 160 200° 240 280 mle TT 13 NMR Spectrum (600 Mz, COC, sokon) rele proton decoupled Lod) ba eee 200 160 120 80 40 0 8{ppm) "HNMR Spectrum (200M, COC soon expansions LY . Je ae em 20 TB em \ \ \ L \ \ 1 1 1 1 109 8 7 6 5 4 3 2 1 0 8 (ppm) 105T T exces 7 i Problem 17 79 IR Spectrum iu my L L 1 \ L L 4000 ‘3000 2000, 1600 1200-800 V (em) 100] n Mass Spectrum sof coke savin No significant UV 3 Mts zoarzoor204 whe absorption above 220 nm 2 20) I CHB 4080 «120 °«160 «200 «240280 mie TI '3C NMR Spectrum (100.0Me, COC: soon) DEPT ci} crf cHP sotvent proton decoupled ’ 1 aan 200 160 120 80 40 (0 (ppm) 1H NMR Spectrum (420M, CDC, soliton) mus J 1 1 \ 1 L \ 1 L \ \ L 10 9 8 7 6 5 4 3 2 o 8 (ppm) 106IR Spectrum Guid fim)! 2959 oad” "3000 3000” 16001200780) V (emt) = 1600) 1200——«800 Mass Spectrum Problem 18 Bee a absorption above 220 nm sake 165860 o7n09 Herc 40 80 120 «160 200 240 280, mie ee eee oa aces Tee 186 NMR Spectrum wGH (500 Ne, COCt,solten) ee wer WOH sctvent proton decoupled eee eee eee par eee warren out, Serpe] ee geet ree seer sen ee ee') 200 160 120 80 40 0 8 (ppm) ‘HNMR Spectrum (200 Wie, COC! zokton) exporslons ms = ao as om 52'S pam 1 1 1 1 L L 1 1 ! \ 1 10 0 9 8 ia 6 5 4 3 2 1 0 (ppm) 107ayy IR Spectrum (lui en) 4000 ‘3000 ‘2000 1600 1200-600 V (om) 8 § 883 ofa peak Mass Spectrum No significant UV absorption above 220 nm Me 14749 CyHgNBr 4060 120 160 200 240 280 mie SA AL 13 NMR Spectrum (100 He, COC, soln) DEPT cHz} crt cHt sotvent proton decoupled i 200 160 120 80 40 0 5(ppm) 1H NMR Spectrum (200 Miz, CDCI, souon) r pm ws L 1 10 9 8 7 6 5 4 3 2 oO (ppm) 108IR Spectrum (KBr disc) 1620 a a a ‘Vv (em) toa i Vas Space oF | OFF mae) : 7 af tere Coty NO, oie coeeok moa oole 2o0 ie Problem 20 No significant UV ‘absorption above 220 nm 186 NMR Spectrum (9000 MHz, 020 sation) DEPT cht cH} CHE proton decoupled 200 160 120 80 40 0 3 (ppm) ‘H_NMR Spectrum (800 Mrz, 220 sutton) Note: there are 3 protons which exchange wah the 020 sobent 38" 37 pom AT J 116 14 ppm HzO and HOD ‘nsovent