TH SCHOOL (VINH CAMPUS)
G12V CHEMISTRY
ANALYTICAL CHEMISTRY
HOMEWORK
NAME ......................................................................................... DATE ..................................
1* A chemist isolates compound L, with empirical formula C3H6O, and sends a sample for analysis.
The analytical laboratory sends back the following spectra.
Mass spectrum
Molecular ion peak at m/z = 116.0.
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H NMR spectra
The numbers next to each signal represent the number of 1H responsible for that signal.
Two 1H NMR spectra were obtained: one without D2O and one with D2O added.
1
H NMR spectrum with no D2O:
Expansion of multiplet
centred at δ 2.7 ppm
2 1 2 1 6
1
H NMR spectrum with D2O added:
2 2 1 6
2
13
C NMR spectrum:
Use the information provided to suggest a structure for compound L.
Give your reasoning. [6]
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2 A chemist uses gas chromatography, GC, to separate the esters in a mixture. The esters are then
analysed using different spectroscopic techniques.
(a) (i) How could the chemist use the results from GC to predict the number of esters in the
mixture and their relative proportions?
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(ii) Why would there be some uncertainty about using GC alone to predict the number of
esters in a mixture?
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(b) The chemist obtains a mass spectrum and a proton NMR spectrum of one of the esters
separated by GC.
• The mass spectrum has a molecular ion peak at m / z = 164.
• The proton NMR spectrum is shown below.
The numbers on the NMR spectrum represent the relative peak areas.
5 2 2
8 7 6 5 4 3 2 1 0
į/ ppm
Analyse this information to identify the ester.
Include full details of your analysis of the proton NMR spectrum.
5
3 A chemist isolates compound H from a mixture and sends it for analysis.
Initial analysis shows that the molecular formula of compound H is C10H12O.
The 13C NMR spectrum of compound H contained eight separate peaks.
The 1H NMR spectrum of compound H is shown below.
1HNMR spectrum
The numbers by each peak are the relative peak areas.
1 4 2 2 3
10 9 8 7 6 5 4 3 2 1 0
chemical shift, ␦ / ppm
(a) The 1H NMR spectrum contains a peak at δ = 0 ppm resulting from a chemical added to the
sample.
State the chemical responsible for the peak at δ = 0 ppm, and state why this chemical was
added to the sample.
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(b) In the 1H NMR spectrum, the peak at δ = 3.7 ppm would normally be expected at a chemical
shift value about 1 ppm to the right, ie at 2.7 ppm.
Use the information in this question to determine the structure of compound H.
Show all your reasoning.
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4 A chemist isolated compound L from the leaves of a common garden herb. He analysed the
compound using a number of techniques.
(a) Compound L contains C, H and O only. Elemental analysis shows that L has the percentage
composition by mass: C, 73.15%; H, 7.37%.
The mass spectrum of L has a molecular ion peak at m/z = 164.
Show that the molecular formula of L is C10H12O2.
[2]
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(b) The 13C NMR spectrum of compound L is shown below.
240 220 200 180 160 140 120 100 80 60 40 20 0
ƣ/ppm
How many different carbon environments (types of carbon) are present in a molecule of
compound L?
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(c) The 1H NMR spectrum of compound L, C10H12O2, is shown below. One of the signals has
been enlarged to help its analysis.
expansion of multiplet
centred at ƣ = 2.7 ppm
5H 1H 6H
8 7 6 5 4 3 2 1 0
ƣ/ppm
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(i) A signal at δ = 0 ppm results from tetramethylsilane (TMS). TMS had been added to the
sample of compound L before the NMR spectrum was run.
State why TMS was added.
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(ii) The 1H NMR spectrum includes an integration trace.
What information can be deduced about compound L from the integration trace?
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(iii) Using the information given in parts (a), (b) and (c) of this question, determine the
structure of compound L.
Show all your reasoning.
In your answer, you should use appropriate technical terms, spelled correctly.
structure of compound L
