UFB Univenitat Autdnoma 102932 STRUCTURAL DETERMINATION ele! EXAM 4, Year 2014-2015 Name: Group: 1. (7 points) Find below the 70 eV El mass spectra of three organic compounds A-C. (a) Assign each spectrum to one of the molecular structures given (1-3). (b) Draw reasonable structures and plausible fragmentation pathways for the fragments whose m/z ratio are given. (c) Aside from fragment peak analysis, which other mass spectrometry experiment could you perform to discriminate between compounds 1-37 so 7 0 105 la eB 8 fal e Ss 2 | 2° ” ye | ge of Shelly obete tors ced n/a = a. es . 3 Relative ierstywit cw = (Cr~|— Or wlz= AAS wr ‘1b uw o 4 12= 92 Stedeou. (A) 4 mw H © Guposnds 4-3 Weve diflercut yclewiler (orenula ova therctore, exack wolewlar wasses- AS A consequence, twey Could be discaminateck by means of highs resclukon NSC HE-NS).2. (8 points) The next figure shows the 'H NMR spectrum (400 MHz, CD;OD) of an organic compound. (a) Fill in the following table with chemical shifts, multiplicities, coupling constants and the assignment of the signals of this organic compound. Please use the numbering given in the structure when assigning the signals in the table. IMPORTANT: Coupling constants should be assigned in the table (e.g. “Juss = 10 Hz). (b) Are you missing any signal in the spectrum? If so, explain what signal is and why it is not observed. 95 90 85 60 75 70.65 60 55 50 45 40 35 30 25 20 15 10 5 (ppm) gg a & a a8 g R xP e rT rT TT pa 7) | | Ju eee OM dL om Ss 798 780 775 748 70 728 750 718 710 5 (ppm) 3.6504 36450 3.6340 36288 36178 36124 36017 3.5963 19797 ~ 1.9689 1.5156 fl i | lly SO 635 63 625 620 365 36 355 200 19 1.60 5 (ppm)(@ Cb) The “H NHR the speckuun because \ at jsdated webnyl OTP Singet & Signals @ dz AS od COO PGH — ves Suk and 3 + % Values consistonk with “trans | deswestitetes Re ad 4 (ge IS.8/6 BRD C2155 ey © a to 3 * Sign @ S=2.46 40 sk shauld COR Ee pH yk @ A stator 3 veins os 3 (6) Cvecalh, the unkrewn moteurter cm aoe at SMould be wode of: . og So on a we DAY ree again