organic chemistry problem set help Below are the 13C and 1H NMR spectra of an un
ID: 1036219 • Letter: O
Question
organic chemistry problem set help
Below are the 13C and 1H NMR spectra of an unknown with the formula C10H2002 1. (1 pt) How many degrees of unsaturation are in this compound? 2. (1 pt) In the IR there is a strong signal at 1720 cm-1. What does this suggest? 3. (1 pt) Does this compound have symmetry? 4. (1 pt) In the 13C NMR, what does the chemical shift of the signal at 175 ppm suggest? 5. (1 pt) In the 1H NMR, what does the integration of the peak at 0.9 ppm suggest? 6. (1 pt) In the 1H NMR, what does the splittina pattern of the peak at 5 ppm suggest 7. (3 pt) What is the structure of this compound? 8. (1 pt) In the mass spectrum, the largest signal (i.e. the base peak) is at 43. Draw one fragment that would give you this signal 180 170 160 150 140 130 120 110 109,"w" ”7060504030"10 9H 6H ?? septet 1H q,1H 5.0 4.5 4.0 3.5 2.5 2.0 1.5 1.0Explanation / Answer
1. Degree of Unsaturation can be calculated as C + 1 - H/2, Hence, for a molecule with molecular formula C10H20O2, DBE = 10 + 1 - 20/2 = 11- 10 = 1.
2. A strong signal at 1720 cm-1 in IR corresponds to an Ester C=O stretch.
3. From the 1H and 13C NMR, it appears the protons and carbons are unequally distributed around ester group, hence, the compound is not symmetric.
4. The chemical shift at 175 ppm in 13C NMR is due to the C=O of an ester.
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