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If the proton is placed in an external magnetic field, the proton's magnetic moment becomes aligned with the external field (lower energy) or against it (higher energy).
Intensity
NMR signal
25
Characteristic Proton NMR Chemical Shifts (ppm) RCH3 RCH2R acyclic RCH2R cyclic 0.9 1.3 1.5 RCCH RNHCH3 RCH2X (X = Cl, Br, I)
O
2.5 23 3.5
9.5 11 13 35
R3CH
R R
O
1.5 2.0
ROCH3, R
3.8
OCH3
N H
59
CH3
1.8
R
R2C=CH2
5.0
ROH
15
2.0 2.3
R CH3
RCH=CR2
5.3
ArOH
47
ArCH3
2.3
ArH
6.5 - 8
RCO2H
10 13
The exact chemical shift for each proton type does not need to be memorized. This table will be provided on an exam if needed. Sample NMR spectra taken from Integrated Spectral Data Base System for Organic Compounds (www.aist.go.jp/RIODB/SDBS/menu-e.html)
1
H-NMR (ppm): 4.19 (singlet; integral = 1.0) 3.41 (singlet, integral = 3.0)
26
H-NMR (ppm): 3.19 (singlet, integral = 1.0) 1.33 (singlet, integral = 1.0)
H-NMR (ppm): 3.43 (quartet, integral = 1.0) 1.68 (triplet, integral = 1.5)
H-NMR (ppm): 3.79 (septet, integral = 1.0) 1.31 (doublet, integral = 6.0)
27
H-NMR (ppm): 3.39 (triplet, integral = 1.0) 1.87 (sextet, integral = 1.0) 1.03 (triplet, integral = 1.5)
H-NMR (ppm): 7.24 - 6.84 (multiplet, integral = 5.0) 5.35 (singlet, integral = 1.0)
H-NMR (ppm): 3.66 (singlet, integral = 1.0) 2.05 (singlet, integral = 1.0)
28
H-NMR (ppm): 5.90 (quartet, integral = 1.0) 2.06 (doublet, integral = 3.0)
H-NMR (ppm): 5.66 (multiplet, integral = 1.0) 1.98 (multiplet, integral = 2.0) 1.16 (multiplet, integral = 2.0)
H-NMR (ppm): 7.38 - 7.00 (multiplet, integral = 1.7) 2.34 (singlet, integral = 1.0)
29
H-NMR(ppm): 10.00 (singlet, integral = 1.0) 7.87 - 7.56 (multiplet, integral = 5.0)
H-NMR (ppm): 5.83 (doublet of doublets, integral = 1.0) 4.93 - 4.82 (multiple, integral = 2.0) 1.00 (singlet, integral = 9.0)
30
Sample Problem #1
C10H14
31
Sample Problem #2
C4H8O2
32