CH217 - NMR accompanying material
Lecture 1: Chemical Shift and Equivalence
For each of the following molecules, decide which protons are equivalent and use this
to predict the number of signals you would see in a 1H NMR spectrum of the
compound:
e)
a)
NO2
b)
f)
c)
NO2
H
H
C
H
H
O
d)
Me
g)
Br
Lecture 2: Predicting Spectra
For each of the following molecules, predict:

the number of 1H NMR signals you expect to see

the “integration” for those signal (ratio of protons)

the position (chemical shift of those signals)

the multiplicity, and approximate J in Hz of the signals
Try to write this information in an appropriate format (δ = ~4.2 (xH, s, CH2XX) ppm)
a)
d)
Br
b)
O
H
H
H
C
O
H
C
H
c)
e)
H
O
in D2O
Br
Lecture 1: Chemical Shift and Equivalence Answers
a) 3
b) 2
c) 2
d) 1
e) 3
f) 3
g) 4
Lecture 2: Predicting Spectra Answers
For each of the following molecules, predict:

the number of 1H NMR signals you expect to see

the “integration” for those signal (ratio of protons)

the position (chemical shift of those signals)

the multiplicity, and approximate J in Hz of the signals
Try to write this information in an appropriate format:
a) δ = ~3.5(1H, s, CH3Br) ppm
d) δ = ~ 4.0(2H, q, J7Hz, OCH2CH3),
~2.0 (3H, s, CH3C(O)), ~ 1.2(3H, t,
J7Hz, OCH2CH3) ppm
Br
b) δ = ~3.5(2H, q, J7Hz, CH2OH),
~1.5 (3H, t, J7Hz, CH3CH2OH), OH
exchanging, ppm
O
H
H
H
O
C
H
C
H
H
O
c) δ = ~1.5(2H, quintet, J7.5Hz,
CH3CH2CH2CH2CH3), ~1.2 (4H, tq,
J7,7.5Hz, CH3CH2CH2CH2CH3), 1.0
(6H, t, J7 Hz, CH3CH2CH2CH2CH3)
ppm
e) δ = ~ 6.0 (1H, ddt, J15, 10, 7Hz,
BrCH2CH=CH2), ~5.6 (1H, dd, J15,
1Hz, BrCH2CH=CH2 trans), ~5.3 (1H,
dd, J10, 1Hz, BrCH2CH=CH2 cis), ~
3.8 (2H, d, J7Hz, BrCH2CH=CH2)
ppm
Br