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Solutions for Nuclear Magnetic Resonance Spectroscopy
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δ (ppm)
C
CH3
CH3 CH2CH3
CH3
H
H
H
H CH3
Br
Cl
CH3CHCH3CH3CH2CH2Cl
CH3
H
H
H H
H
C
O
CH2 C
O
CH3OC
CH3
H3C
CH3
3H
2H
9H
TMS
H H
HH
CH3O OCH3
CH3 C
CH3
OH
C C H
five types of H
three types of H
two types of H
three types of H
c
c
b
b
bb
a
a
a
a
a
e
d
c b a
(f)
(c)(b)(a)
3
4
(a)
c
b
a
d
c
b
four types of H
(b) The three types of aromatic hydrogens appear in a relatively small 
space around δ 7.2. The signal is complex because all the peaks from 
the three types of hydrogens overlap.
5 c
a b
c
a
b
Note: NMR spectra drawn in this Solutions Manual will represent peaks as single lines. These lines 
may not look like "real" peaks, but this avoids the problem of variation among spectrometers and 
printers. Individual spectra may look different from the ones presented here, but all of the important 
information will be contained in these representational spectra.
c
6 The three spectra are iden tified with their structures. Data are given as chemical shift values, with the 
integration ratios of each peak given in parentheses.
Spectrum (a)
bb
a a
aa
a = δ 6.8 (2) (4H)
b = δ 3.7 (3) (6H)
a
b
c
a = δ 2.4 (1) (1H)
b = δ 2.6 (1) (1H)
c = δ 1.5 (6) (6H)
Spectrum (b)
c
c
two types of H
b
a
(d)
HC CH
CH3
CH3H3C
H3C
a
a a
b
Br
CH3
H
HH
H(e)
a a
b b
c
three types of H
290

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