40 marks 6 section b comprehensive spectroscopic

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(40 marks)
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6 Section B (Comprehensive spectroscopic analysis) Answer all questions in this section in the answer book. (Total 60 marks) 21. Based on all of the following spectroscopic data of an unlmown compound with molecular formula C 7 H 8 0, (I) determine the chemical structure of this compound; (2) assign all the peaks in the 1 H NMR spectrum . lR Spectrum (liquid film) 4000 3000 100 80 l 60 ~ 40 0 20 I 1 " 40 78 80 t J c NMR Spectrum (100 MH<:, CDCl 3 solution) DEPT-135 proton decoupled 200 1 H NMR Spectrum {400MHz, CDCI 3 solullon} expansion 11 7.2 7.0 6.8 2000 1600 v (crri 1 ) M+· 1oa 93 I 120 160 200 m le I I I ltl 160 120 r-- ,..-' pp m ~ - 10 9 8 7 6 . r(\ rr 1200 BOO Mass Spectrum 240 280 solvent I 80 40 0 o (ppm) f------ TMS - ' ' 5 4 3 2 0 a (ppm) (10 marks)
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7 22. Based on all of the following spectroscopic data of an unknown compound with molecular formula C 6 H 10 0 4 , (I) determine the chemical structure of the compound; (2) assign all peaks in the 1 H and 13 C NMR spectra. IR Spectrum (liquid film) 4000 3000 I I 13 c NMR Spectrum (50.0 MHz, CDC! 3 solution) DEPT-135 Proton decoupled I I 200 1 H NMR Spectrum (200 MHz., CDCt 3 solution) "'-.!. I 10 9 I I I 8 2000 1600 V (cni 1 ) 1200 ' I I I I I I 160 120 I I I 7 6 5 800 I I I I I I solvent w I I I I 80 40 0 1i (ppm) 1 ,-- ~L - TMS .11. I I I 1 I I 4 3 2 1 0 () (ppm) (10 marks)
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8 23. Based on all of the following spectroscopic data of an unknown compound with molecular formula C 10 H 12 0, (1) determine the chemical structure of the compound; (2) identify the fragment ions that correspond to the peaks with m/z = 120, 106, 105 and 77 in the EI-MS spectrum. (3) show the fragmentation processes involved in the formation of these ions (m/z = 120, 106, 105 and 77). IR Spectrum 1 (liquid film) 4000 3000 13 C NMR Spectrum (50.0 MHz, CDCI 3 solution) proton decoupled I 200 1 H NMR Spectrum (200 MHz, CDCI 3 solution) ' ' I I ' ~ .i J :! ~------~ l lO 9 8 1686 ' 2000 1600 V (cni 1 ) I 160 _j 3.0 7 6 '" " ' 800 1200 .J I .. 100 tr . " m/:. ~xpansion I 135 130 ppm ~solvent 11 120 80 40 0 o (ppm) expansion 2.0 1.0 pp m TMS 5 4 3 2 1 0 o (ppm) (10 marks) M (1r
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9 24. Based on all of the spectroscopic data of an unknown compound with molecular formula C6Hs0, (!) determine the chemical structure of the compound; (2) assign all peaks in the 1 H and 13 C NMR spectra.
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