Question

62 5.1. Spectral Data for synthesis of a Therapeutic Agent IR spectrum 3190 47 167s 1329 13 033 29 726 38 3074 84 5 S5 15 2956 52 1500 25 254 855 66 657 269e 79 487 ID 1217 7 949 22 663 67 2855 79 1441 B 1159 12 810 62 ssi 38 1336 84 403 49 J135 30 801 52 512 55 (818 84 1330 1091 12 767 13 431 70 KAVENUNIEERI -1 Mass spectrum 80- 60 40 20 25 100 125 150 m/ Z Experiment 5
Annotate the 13C, 1H, and IR spectra of the therapeutic agent

Answer 1

From IR data, there is a signal for carboxylic group (due to broad signal at region 3100-3500 cm-1) which is confirmed from additional signal at 1600-1700 cm-1 and peaks at 170 ppm and 10-11 ppm in 13C and 1HNMR respectively.

From 13C NMR, thotal number of signals are 8 which indicates the presence of 8 non-equivalent carbons in the molecule. Peak at 55-60 ppm belongs to a CH3 attached to O atom [ie. OCH3 group] and peak at 160 ppm indicates carbon attached to a O atom. Further, 1HNMR shows 4 signals for 4Hs in aromatic regions (6-9 ppm) means the aromatic ring is disubstituted but not symmetrically. The peak at 10-11 ppm belongs to OH of COOH functionality.

Based on these informations the structure of compound can be give as below which is varifying the m/z value at 152 as M+ peak in mass data.

13C NMR spectrum 63 200 180 160 140 120 100 80 60 40 20 o H NMR spectrum CH3 singlet, 3H both peaks are merged doublets of doublet, 1H ex multiplet, 1H. multiplet, 1H f singlet, 1H doublets of b doublet, 1H 3H Integration 1H 1H 2H 1H 11 10 9 8 7 6 5 4 3 2 1 ppm