I i i i v rr 0 100 68 mass spectrum 80 ro 0 60 0 ro d

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I I I I ;, 'V ~ rr 0 100 68 Mass Spectrum 80 ~ ro 0 ~ 60 0 " ro D 40 15 M+·= 96 "' 20 IR Spectrum 11 .I I C 6 H 8 0 {liquid film) 1685 I I I I 40 80 120 160 200 4000 3000 2000 1600 v (cm 1 ) 1200 800 m le I I I I I I I I I I 13 c NM R Spectrum (1 00.0 MHz, CDCI 3 solution) DEPT-135 I 11 Proton decoup!ed solvent I I ' I I I I I I 200 160 120 80 40 0 ll (ppm) 1 H NMR Spectrum ( 400 MHz, CDCI 3 solution) 6.9 6.8 ppm 5.90 5.85 ppm 2.4 2.2 ppm 1.9 1.8 ppm - - TMS I - - -; 10 9 8 7 6 5 4 3 2 1 0 o (ppm) (10 marks)
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10 25. Ibuprofen is a non-steroidal anti-inflammatory drug (NSAID) used for the relief of symptoms of fever, as a pain killer. Based on all of the following spectroscopic data of ibuprofen, (1) determine the chemical structure of ibuprofen; (2) assign all peaks in the 1 H NMR spectrum; (3) draw the structure of the fragment ion with m/z = 91 in the El-MS spectrum. El-MS 100 80 20 0 IR ,. 4000 13 CNMR MYJ~-2-l"lS I, & ,, d .. ,. .. , . 20 40 60 3000 I ' 163 161 (100%) {96.9%) 91 M 206 119 {46.7%} (42.3%) (45.9%) 107 (28.1%) 207 {6.6%) 1, .!I ,,, / I . .. , . 80 100 120 140 160 180 zoo 220 """ 1721 2000 I'"!N /"- <.0 G!C! '<!; "1 or-- C"l r-- o:tM N N ........................ 11 I) ' mjz ,.-/1 1500 ~m rrrnn w 1000 500 cm- 1 ' ' ' zoo 180 160 140 120 100 80 60 40 20 0 COS-11-007 r:pm
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11 -~--~--+------~~~-~-~-- ----b-----~---_J-+Ii,-----+---_-----~ l I J I ~, 8 6 5 4 3 2 0 I/ ( _.) / ( J I ,..r:== - - I- ][ I~ \ .... 7 3 2 1 (10 marks)
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12 26. Based on all of the following spectroscopic data of an nnknown compound, (1) determine the chemical structure of the compound; (2) assign all peaks in the 1 H NMR spectrum; (3) explain the splitting pattern of the proton signal that appears between 2.0 - 2.5 ppm, and draw the tree diagram as part of your answer. MASS 391411 50 40 45 IR lOO " u " "' .E E ~ " I!! 50 1- ;,:: 50 I "' "' "' "' 55 ,!,';:>,"<, ''"" ~ ~ .... ~ "'"" ~ 60 m/z 65 ,!, .., "' "' 4000 3000 2000 1 H NMR 300 MHz Wavenumber (cm ·•) j_ 1280 1260Hz 680 660Hz 4.0 3.5 3.0 2.5 13 C NMR 75.5 MHz COC!, I I I I I 77.0 76.5 ppm 78.0 77.5 11 95 90 85 80 75 70 65 60 55 50 45 40 DEPT-90 DEPT-135 -END OF PAPER- 70 75 80 85 I I I I I l .!.. :;;; ;:;t::;:: 8 :!: ~ - "'..., ~ "'~ ~ 1000 2.0 1.5 ppm 11 35 30 25 20 pp m (10 marks)
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- hJdrogerJ 1 H 1.0079 ~tlllum beryllium 3 4 Li Be &.941 9.0122 sodium 111<1gneslum 11 12 Na Mg 22.990 24.305 potassium cntctum scondium ll!lmium 'lilnarJium chromium rnmgc111ese Iron cob,1lt 19 20 21 22 23 24 25 26 27 K ea Se Ti V Cr Mn Fe Co 39,098 40.078 44.956 47.867 50.942 51.996 54.93-9 55.845 5B.933 rubidium strontium yttrium zirconium niobium molybdenum technetium ruthenium rho:lium 37 38 39 40 41 42 43 44 45 Rb Sr y Zr Nb Mo Tc Ru Rh 85.468 87.62 R8.906 91.224 92.906 95.94 1981 101.07 102.91 c8eslum bmium lutetium hJfnlum !Jnblum tungsten rhenium osmium Iridium 55 56 57-70 71 72 73 74 75 76 77 Cs Ba * Lu Hf Ta w Re Os · lr 132.91 137.33 174.97 178.49 1B0.95 18:3.84 186.21 180.21 192.22 rr::mclum r8dium lawrencium rulherfordlllm dubnlum seaborglum
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