Problem 2 - Predict a reasonable structure from the spectral information provide
ID: 986031 • Letter: P
Question
Problem 2 - Predict a reasonable structure from the spectral information provided below. As much as possible match the spectral information to the part of the structure that it explains. Show your work. Interpret as fully as possible from structure. Not every peak is interpretable. (units = cm IR Spectrum: Interpret as fuly as IR Spectrum MS data exact mass 3340 163011 1380 Mt2-2996 1050 750 1735 2960-2850 1470 1230 4000 3500 3000 2500 2000 1500 1000 500 Proton NMR: interpret data (calculate chemical shifts to confirm they match actual values, N- #neighbors) 3.24 3H,s 1H,brd s 2.0 J127 2H 1H,dd J-12,7 3.91 Hdd J12,7 2.16 H,oct 1.08 3H.d 4.03 1H.dd J-12,7 1H.t 1.44 7.88 7.35 688 2.42 1H,oct J#7 PPM 1"C and DEPT NMR: As much as possible match the "C peaks to carbons in your structure. Top spectrum-DEPT-135NMR-CHs and CH appear (up) and CH2 appears (down) 166.0 158.0 133.7 200 190 18° 170 160 150 140 130 120 110 100908070605040302° t |1203 113.3 Middle spectrum-DEPT-90BC NMR-oaly C-H appears (up) 200 190 180 170 160 150 140 130 120 110 100%8070605040"2010 60.4 59.3 Botom spectrum-proton decoupled 'c NMR spectrum - shows all types of carhon 29.2 27.1 17.9 16 9x2 200 190 180 170 160 150 140 130 120 110 100 90 30 50 40 20 10Explanation / Answer
Our first important data MW= 324.2
From the 1H spectrum you could say that it is an aromatic compund, but i can not see the aromatic overtones in the IR spectrum. It may be there are some C=C with some aromatic characteristics but there are not exactly aromatic.
With the 13C spectrum you can deduce that there are 16 C and that 7 are C-H, 3 are CH3 and 4 are CH2.
I can´t really see the numbers in the integration of the H of the 1H spectrum, but you can count them and have an average number of protons in your compound.with the average Weight of the carbons and the protons that you can calculate from de NMR spectrum you can make a aproximation of what other atom is in your compound due to the relation with the MW of the entire compound.
From the HMBC correlation spectrum you can deduce that all the C that appear on the high zone are quaternaries. So they should have four different substituyents on them.
According to the signals of the IR you can see there is an oxygen present in the molecule. but you will not know if it is a carbonile or an alochol until you calculate the number of insaturations.
And when you have an aproximate of what are the components in your compound you can calculate the numbers of insaturations and you will have exactly how you can build your molecule.
Hope this works for you!
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