Experiment 14.ppt

Experiment 14: IR AND NMR IDENTIFICATION OF AN UNKNOWN Objectives: To learn how to interpret IR and NMR spectra. To use IR and NMR spectra to propose a structure for an unknown, given the molecular formula. Before coming to lab… Go to the website: From the left menu, select TUTORIALS. From the right column, PRELECTURES, scroll ? of the way down the page. Watch the following: SPECTROSCOPY (Part 3 of 4) SPECTROSCOPY (Part 4 of 4) (YOU’LL BE GLAD YOU DID! ?) IR SPECTROSCOPY THINGS TO CONSIDER… What kinds of bonds do I have? If they appeared in the IR spectrum, where would they be? Now, look at the spectrum. Are they there? IR SPECTROSCOPY IR SPECTROSCOPY Base values for Absorptions of Bonds (cm-1) O-H 3200-3600 C-O 1000-1200 (Esters have two!) C-H (sp2) 3000-3100 C-H (sp3) 2850-3000 Aldehyde C-H 2700 2800 (there are two!) Amide N-H 3150-3350 C=O 1650-1740 C-X 500-700 Full IR Absorption Correlation Table in Appendix J CALCULATING DEGREE OF UNSATURATION CcHhNnOoXx DU = (2c + 2) – (h – n + x) 2 1o unsaturation = 1 C=C or 1 ring 2o unsaturation = 2 C=C, 2 rings, or CΞC, or combination of C=C rings 3o unsaturation = combination of double bonds, triple bonds, rings 4o unsaturation = typically indicates an aromatic ring 13C-NMR SPECTROSCOPY Information provided: Functionality (Chemical Shift) tells the type of carbon via position of signal on x-axis Presence of symmetry via # of signals Presence of non-protonated carbons via small signals sometimes useful, not always! TYPICAL CHEMICAL SHIFTS 190-220d aldehydes, ketones 160-190d esters, amides, carboxylic acids, acyl halides 110-160d arenes, alkenes 50-110d alkynes, sp3C attached to functional groups 0-50d sp3C-Csp3, where 4o3o2o1o 13C NMR CHEMICAL SHIFT CORRELATION CHART p. 118 in lab manual 1H-NMR SPECTROSCOPY Information provided: A. Functionality chemical shift tells the type of hydrogen Via position on x-axis B. Presence of symmetry via the # signals C. N