O

C O
H3C C CH3 1-methoxypropan-2-one
H H

peak peak peak

for CH2 for CH3 for CH3
integration relative
curve heights of the
integration
curves is
2:3:3

4.0 3.0 2.0

Chemical shift, (ppm)

10.5.1.1 Chemical shifts

~4.5 ppm ~3.5 ppm ~3.4 ppm ~3.2 ppm

R–CH2–F R–CH2–Cl R–CH2–Br R–CH2–I

Decreasing electronegativity
of the halogen atom
 Functional group (ppm)

alkane CH–C 0–1.5

allylic, benzylic CH–C=C 1.5–2.5

halogenoalkane CH–X
amine CH–NR2 2.5–4.5
ether CH–OR
alcohol CH–OH

alkene CH=C 4.5–6.5

aromatic CH=C 6.5–8

aldehyde CH=O 9–10

~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

~3.6 ppm ~4.1 ppm ~4.9 ppm

O O O
CH3 CH2R CHR2
H3C O RH2C O R2HC O

~2.0 ppm ~2.3 ppm ~2.5 ppm

Aromatics, alkenes and aldehydes

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

10.5.1.2 Spin-spin splitting or coupling

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

7.0 6.0 5.0 4.0 3.0 2.0 1.0

Chemical shift, (ppm)

Alkane carbons (ppm) Functional group (ppm)

CH3 5–20 halogenoalkane C–X 0–80
CH2 20–30 alcohol/ether C–O 40–80
alkene C= 100–150
CH 30–50
aromatic C= 110–160
C 30–45
carbonyl C=O 160–210