Fig. 13.1

NMRIRUV

Fig. 13.2NMR: excited spin stateIR: excited vibrational stateUV: excited electronic state

Fig. 13.30

Tab. 13.4

Fig. 13.31

“fingerprint region”

Fig. 13.32

Fig. 13.33

Fig. 13.34

Fig. 13.35

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

OH

O

CH3

O

OH OH

IR: Isolation of Cinnamon Oil from CinnamonExp. [11C]

Mayo, pp. 213 – 218. Please note the prior reading assignments given on p. 213.

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 – http:wiley.com/college/chem/mayo321850/wave_s.html(under Reference Discussions pp. 27-30)

Fig. 13.1

NMRIRUV

Fig. 13.2NMR: excited spin stateIR: excited vibrational stateUV: excited electronic state

Fig. 13.3

• The lower energy orientation is the oneparallel to Ho and more nuclei havethis orientation.

Fig. 13.4• The energy difference in the two spin statesis proportional to the strength of the appliedfield.

4.7 Tesla - 200MHz (radiofrequency)

Fig. 13.5

Source of energyto excite nucleus

Aligns nuclear spins

Contains sample,may have deuteratedsolvent

Detects theabsorption of rf radiation

Fig. 13.23a

• 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. 13.6

• Alone, a proton would feel the full strengthof the external field, but a proton in anorganic molecule responds to both theexternal field plus any local fields withinthe molecule.

• Electrons “shield” the proton from thefull effects of the magnetic field.

Chemical Shift

Fig. 13.7 • Electron density “shields” theproton from the full effects ofthe external magnetic field.

H-C-CH-C-XH-C=CH-ArH-C=O

Chemical Shift

Tab. 13.1

H-C-X 2-5 ppm

Chemical Shift

Fig. 13.11

Integration

Integration

C8H8O2

http://www.chem.ucla/~webspectra

Fig. 13.12

Multiplicity

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

Fig. 13.15

C2H5Br

2

3

Deduce structure of :

Fig. 13.17

1 H

6 H

Deduce structure of C3H7Cl

C8H8O2

GO TO web site

Fig. 13.19

Fig. 13.20

Fig. 13.21

-OH protons areexchangeable

Fig. 13.22

Tab. 13.3

Fig. 13.23b

Fig. 13.24

Fig. 13.25

Fig. 13.26a

Fig. 13.26b

Fig. 13.28

Fig. 13.29

Fig. 13.37

Tab. 13.5

Fig. 13.38

Fig. 13.39

Fig. 13.40

+ e- .+ + 2e-

M+

base peak

Fig. 13.41

chlorobenzene

Fig. 13.42

decane base peakM+

molecular ion peak

Fig. 13.43

propylbenzene

Fig. 13.44

GC-MS

Spectra for homework problems at the end of Chapter 13 -

Fig. 13.45

Fig. 13.46a

Fig. 13.46b

Fig. 13.47a

Fig. 13.47b

Fig. 13.48a

Fig. 13.48b

Fig. 13.49a

Fig. 13.49b

Fig. 13.49c

Fig. 13.49d