3) C,H1,N2 13C NMR IR LUU ppm 62.65 45.53 39.79 4000 3000 2000 L000 NAVENUNBERl 200 180 160 140 120 100 80 60 40 20 1Η NMR Cos-03-942 ppm Assign. Shift(ppm) 3 A 1.40 В 2.228 Exchanges w/ D20 C 2.341 2.764 1 TMS 1 Impurity 1 6 4 3

1. Given the following 'H NMR spectra. A. Draw structure of compound. В. Label peaks (Ha, Hb, He, etc.) and indicate multiplicity. Benzene 10 8 7 6. 5 4 3 2 1 ppm HPM-00-113

Name the compound

Comparison of specific functional group diagnostic peaks (C=O carboxylic acid, C-H, O-H carboxylic acid, O-H phenol, C=C) between Literature and Experimental spectra.

D. explain each step with words on how to get the structure. Step 1: Calculate the Index of Hydrogen Deficiency (IHD). Step 2: Use IR to determine obvious functional groups. Step 3: Use 1H-NMR to determine structural details.  Step 4: Confirm the final structure using 13C-NMR.

Question 25

The proton NMR and IR spectra of an unknown compounds is shown on the next page. Using the molecular formula C5H12O, find L a) the index of saturation b) the structure of the unknown compound c) assign the absorption bands to the functional groups in the IR spectrum d) label all peaks in the NMR spectrum, and label the same peak on the hydrogens in the structure Transmittance (%) 100 80 60 40 20 0 3500 CT TYCE Tabdf62 2874.30 2500 Wavenumber (cm-¹) 3000 2000 1466.09 1500 1307.78 1124.04 21 seser 908.46 1000 37.21

Use the following compounds to match its IR spectrum

draw the ethanol strcture and  then circle the protons on the structures and correlate the 1H's to the resonances (peaks) on the 1H NMR spectra.