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10.5.1.1 Chemical Shifts
10.5.1.1 Chemical Shifts
C O
H3C C CH3 1-methoxypropan-2-one
H H
Decreasing electronegativity
of the halogen atom
Functional group (ppm)
halogenoalkane CH–X
amine CH–NR2 2.5–4.5
ether CH–OR
alcohol CH–OH
~2.0 ppm H H
~2.3 ppm ~3.1 ppm
~5.0 ppm
H2 H3C CH2 CH2Br
C CH2
H3C C ~3.6 ppm
H
H H
~1.0 ppm
~5.8 ppm ~7.2 ppm ~7.0 ppm
small induced
ring current magnetic field
small induced (circulating
magnetic field B i circulating
electrons) electrons
Bi
R
H C O
H
applied applied
B0 magnetic B0 magnetic
field field
number of peaks
( + 1) peak pattern integration ratios
0 1 singlet (s) 1
1 2 doublet (d) 1:1
2 3 triplet (t) 1:2:1
3 4 quartet (q) 1:3:3:1
4 5 quintet (quin) 1:4:6:4:1
5 6 sextet (sex) 1 : 5 : 10 : 10 : 5 : 1
6 7 septet (sep) 1 : 6 : 15 : 20 : 15 : 6 : 1
H H
C triplet for
H3C CH3
2 × CH3
propane
septet
for CH2 relative
heights of the
integration
curves is 1 : 3
1.5 1.0
Chemical shift, (ppm)
identical (H = H)
Replace H Replace H
Z H with Z H H with Z H Z
C C C
Cl Cl Cl Cl Cl Cl
not identical ( H H)
Replace H Replace H
Cl Z with Z Cl H with Z Cl H
C C C C C C
Me H Me H Me Z
Alkenes
Aromatics
Alcohols
10.5.1.3 Summary
peak
HA hydrogen / ppm appearance
HB O HD HD
HB HE HA 7.64* doublet (J = 16 Hz)
O HB 7.30–7.14 broad multiplet
HE HE
HB HB HC HC 6.39 doublet (J = 16 Hz)
HB HD 4.19 quartet (J = 7 Hz)
ethyl (E)-cinnamate HE 1.30 triplet (J = 7 Hz)
*This alkene hydrogen is deshielded
because of conjugation with the
(electron-withdrawing) carbonyl group.
HA + HB HE
HD
HC