1h#nmr’spectroscopy’worksheet’ part’i’ · 2013-02-11 ·...
TRANSCRIPT
1H-‐NMR Spectroscopy Worksheet
Part I
For each of the molecular formulas shown below calculate the index of hydrogen deficiency (IHD). In addition, suggest three possible chemical structures that are consistent with the degree of unsaturation.
a) C7H14O2
b) C4H10O
c) C9H10O
d) C8H9NO3
e) C4H6O2
f) C7H10Cl2
Part II
For each of the following chemical structures a 1H-‐NMR spectrum is provided on the following 3 pages. Match each compound with its 1H-‐NMR spectrum. Draw the structure above the corresponding spectrum and clearly assign the chemical shifts to the appropriate protons on the molecule.
CH2CH3
OCH3
OH
O
OH
O
Br
O O
O O
O O
O O
Br
p-ethylanisole
1-propanol
3-methylbutanal
butanoic acid 2-bromobutane diethyl malonate
1-pentene
diethyl ethylmalonate
1-bromopropane
0.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.0
3.0 3.0
2.0
1.0 1.651.701.751.801.851.90
4.004.054.104.154.20
0.81.01.21.41.61.82.02.22.42.62.83.03.23.43.6
3.0
2.0 1.0 2.0
1.301.401.501.601.701.80
2.202.222.242.262.282.302.32
0.81.01.21.41.61.82.02.22.42.62.83.03.23.43.6
3.0
2.0
2.0
1.601.701.801.902.002.102.20
0.40.60.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.85.05.2
5.9
0.9
2.0
9.709.729.749.769.789.809.82
1.0
2.002.102.202.302.402.50
ppm
1.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.64.8
6.0
2.0 4.0
ppm
2.02.53.03.54.04.55.05.56.06.57.0
3.0
2.0
3.0
2.0 2.0
ppm
0.40.60.81.01.21.41.61.82.02.22.42.62.83.03.23.43.6
2.0 2.0
3.0
Offset @ 11.8 ppm broad singlet
ppm
Integration 1.0
0.81.01.21.41.61.82.02.22.42.62.83.03.23.43.63.84.04.24.44.6
3.0
6.0
2.0
1.0
4.0
ppm
1.01.52.02.53.03.54.04.55.05.5
1.0
2.0 2.0
1.9
3.0
ppm
0.800.901.001.101.201.301.401.501.60
5.005.205.405.605.80
Part III
Shown below are the structures of two esters. They are isomers and the only difference between the two compounds is the orientation around the ester functional group. We have provided the 1H-‐NMR of each ester in the next page.
1) Match each compound with its 1H-‐NMR. 2) Draw the structure above the spectrum and assign the protons to their appropriate chemical
shifts.
O
O
O
O
benzyl propionate ethyl phenylacetate
1.01.52.02.53.03.54.04.55.05.56.06.57.07.5
3.0
2.0
2.0
5.0
ppm
1.01.52.02.53.03.54.04.55.05.56.06.57.0
4.9
2.0
2.0 3.0
ppm
Part IV The 1H-‐NMR spectra of the following pages represent mono, di and trisubstituted aromatic compounds. Also included are disubstituted compounds as ortho, meta and para. The compounds representing each spectrum are shown below.
a) Match each 1H-‐NMR spectrum to its compound. b) Draw the chemical structure above the spectrum and indicate the protons on each chemical
shift. You do not have to assign each specific peak on the aromatic region.
Cl
O
O2N
CH2CH
CH3
CH3CH3
CH3
O
OH
O
CH3
OH
OH
NO2
OH
NO2
OH
NO2
2-chloro-5-nitrobenzaldehyde Isobutylbenzene m-xylene
o-nitrophenol m-nitrophenol p-nitrophenol
o-vanillin phenol
5.05.25.45.65.86.06.26.46.66.87.07.27.4
5.1
1.0
ppm
6.706.806.907.007.107.207.30
2.0
1.0
2.0
2.53.03.54.04.55.05.56.06.57.0
6.0
3.0
1.0
ppm
6.706.806.907.007.107.207.307.40
3.0
1.0
6.87.07.27.47.67.88.08.28.48.68.89.09.29.49.69.8
1.0 1.0 1.0
Offset @ 10.5 ppm singlet
ppm
Integration 1.0
8.408.508.608.708.808.90
1.01.52.02.53.03.54.04.55.05.56.06.57.07.5
5.0 2.0
1.0
6.0
ppm
6.26.46.66.87.07.27.47.67.88.08.28.4
1.0 1.0 1.0 1.0
Offset @ 10.6 ppm broad singletIntegration 1.0
ppm
4.04.24.44.64.85.05.25.45.65.86.06.26.46.66.87.07.27.47.6
3.0
1.0 2.0
Offset @ 11.2 ppm broad singletIntegration 1.0
ppm
9.709.759.809.859.90
1.0
5.65.86.06.26.46.66.87.07.27.47.67.88.08.28.48.68.89.09.2
2.0 2.0
Offset @ 10.7 ppm broad singletIntegration 1.0
ppm
6.807.007.207.407.607.80
1.0
1.0
1.0
1.0
Offset at 10.3 ppm small broad singletIntegration 1.0