This question is about compound Z, with molecular formula C7H12O3
1.
Figure 1 shows the infrared spectrum of Z.
Figure 1
(a) Identify the bond that causes the absorption at 1725 cm–1
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Figure 2 shows the 13C NMR spectrum of Z.
Figure 2
(1)
(b) How many different carbon environments are there in a molecule of Z?
5678
Tick ✓ one box
(1)
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(c) State the type of carbon environment that causes the peak at = 174 ppm
Use Table C in the Data Booklet to help you answer this question.
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(d) the table below shows data from the 1H NMR spectrum for compound Z.
Chemical shift / ppm 4.10 2.60 2.56 2.19 1.26
Integration ratio 2 2 2 3 3
Splitting pattern quartet triplet triplet singlet triplet
Explain what can be deduced from the splitting patterns and chemical shift values for
the peaks at = 4.10 ppm and at = 1.26 ppm
Deduce the part of the structure of Z that causes the peaks at
= 4.10 ppm and = 1.26 ppm
Use Table B in the Data Booklet to help you answer this question.
Peak at = 4.10 ppm
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Peak at = 1.26 ppm _________________________________________________
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Part of structure
(5)
(e) Deduce the part of the structure of Z that causes the peak at = 2.19 ppm
Part of structure
(1)
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1
Figure 3 shows the H NMR spectrum of compound Z.
Figure 3
(f) Suggest why it would be difficult to determine the structure of Z using the spectrum
in Figure 3, without the information in the table in part (d).
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(g) Deduce the structure of Z.
(1)
(Total 11 marks)
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This question is about NMR spectroscopy.
2.
(a) A compound is usually mixed with Si(CH3)4 and either CCl4 or CDCl3 before recording the
compound’s 1H NMR spectrum.
State why Si(CH3)4, CCl4 and CDCl3 are used in 1H NMR spectroscopy.
Explain how their properties make them suitable for use in 1H NMR spectroscopy.
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(6)
(b) Deduce the splitting pattern for each of the peaks given by the H atoms labelled x, y and z
in the 1H NMR spectrum of the compound shown.
x _____________________________________________
y _____________________________________________
z _____________________________________________
(3)
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(c) Suggest why it is difficult to use Table B in the Data Booklet to predict the chemical shift (δ
value) for the peak given by the H atom labelled y.
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(1)
(d) Two isomers of CH3CHClCOCH(CH3)2 each have two singlet peaks only in their 1H NMR
spectra.
In both spectra the integration ratio for the two peaks is 2:9
Deduce the structures of these two isomers.
Isomer 1
Isomer 2
(2)
(Total 12 marks)
Which amine has only three peaks in its proton NMR spectrum?
3.
A Methylamine
B Trimethylamine
C Diethylamine
D Propylamine
(Total 1 mark)
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N.m.r. spectroscopy can be used to study the structures of organic compounds.
4.
(a) Compound J was studied using 1H n.m.r. spectroscopy.
(i) Identify a solvent in which J can be dissolved before obtaining its 1H n.m.r. spectrum.
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(ii) Give the number of peaks in the 1H n.m.r. spectrum of J.
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(iii) Give the splitting pattern of the protons labelled a.
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(iv) Give the IUPAC name of J.
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(b) Compound K was studied using 13C n.m.r. spectroscopy.
(i) Give the number of peaks in the 13C n.m.r. spectrum of K.
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(1)
(ii) Use Table 3 on the Data Sheet to suggest a δ value of the peak for the carbon
labelled b.
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(1)
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(iii) Give the IUPAC name of K.
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(Total 7 marks)
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