Fig NMRIRUV

Fig NMR: excited spin state IR: excited vibrational state UV: excited electronic state

Fig

Tab. 13.4

Fig “fingerprint region”

Fig

Fig

Fig

Fig

Which one of the following compounds is most consistent with the IR given?

IR: Isolation of Cinnamon Oil from Cinnamon Exp. [11C] Mayo, pp. 213 – 218. Please note the prior reading assignments given on p Your write-up should include the following: Data from the experiment including mass of oil, percent recovery from cinnamon, IR spectrum. Structure of cinnamon oil, with an analysis of the IR spectrum. Problems 6-77, 6-78, 6-79, 6-80 Steam Distillation – (under Reference Discussions pp )

Fig NMRIRUV

Fig NMR: excited spin state IR: excited vibrational state UV: excited electronic state

Fig The lower energy orientation is the one parallel to H o and more nuclei have this orientation.

Fig The energy difference in the two spin states is proportional to the strength of the applied field. 4.7 Tesla - 200MHz (radiofrequency)

Fig Source of energy to excite nucleus Aligns nuclear spins Contains sample, may have deuterated solvent Detects the absorption of rf radiation

Fig a Number of signals – number of nonequivalent protons (H) Chemical shift – electronic environment of the proton, represented by ppm Integration – number of equivalent protons (H), represented as area beneath the curve Multiplicity – number of protons (H) on the adjacent positions

Fig Alone, a proton would feel the full strength of the external field, but a proton in an organic molecule responds to both the external field plus any local fields within the molecule. Electrons “shield” the proton from the full effects of the magnetic field. Chemical Shift

Fig Electron density “shields” the proton from the full effects of the external magnetic field. H-C-CH-C-XH-C=CH-ArH-C=O Chemical Shift

Tab H-C-X 2-5 ppm Chemical Shift

Fig Integration

C8H8O2C8H8O2

Fig Multiplicity n+1 Rule - A signal is split into n+1 peaks, where n=number of adjacent protons (H)

Fig C 2 H 5 Br 2 3 Deduce structure of :

Fig H 6 H Deduce structure of C 3 H 7 Cl

C8H8O2C8H8O2 GO TO web site

Fig

Fig

Fig OH protons are exchangeable

Fig

Tab. 13.3

Fig b

Fig

Fig

Fig a

Fig b

Fig

Fig

Fig

Tab. 13.5

Fig

Fig

Fig M+ base peak

Fig chlorobenzene

Fig decane base peak M+ molecular ion peak

Fig propylbenzene

Fig GC-MS

Spectra for homework problems at the end of Chapter 13 -

Fig

Fig a

Fig b

Fig a

Fig b

Fig a

Fig b

Fig a

Fig b

Fig c

Fig d