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H
H
OH
H
C
H
OH
C
H
C
H
H
C
H
C
H
H
Q1
Which molecule has an odd number of peaks in its 13C NMR spectrum?
A
D
O
O
O
MgCl
Q2
A structural isomer of C5H11OH has a significant peak in its mass spectrum with an m / z value of 31.
Its 13C NMR spectrum shows four different peaks.
What is the isomer?
Q3
3-methylbutan-1-ol
3-methylbutan-2-ol
pentan-1-ol
pentan-2-ol
The diagram shows the 13C NMR spectrum of an alcohol of formula C4H10O.
80
60
ppm
butan-1-ol
butan-2-ol
2-methylpropan-2-ol
2-methylpropan-1-ol
40
20
Q4
Dioxins can be formed during the combustion of chlorine-containing compounds in waste incinerators.
Dioxins are very unreactive compounds and therefore remain in the environment and enter the food chain.
Many dioxins are polychlorinated compounds such as tetrachlorodibenzodioxin (TCDD) shown below.
CO
CO
CO
CO
13
C n.m.r.
13
H
H
H
C
H
Si
H
H
C
H
Si(CH3)4
H
C
O
C
O
ethanoic acid
Q5
The
H C
H C
O
C
O
13
C NMR spectrum of a compound with formula C4H8O2 shows peaks at 15 ppm, 20 ppm,
CH3COOCH2CH3
H
H
B
butanoic acid
propanoic acid
HCOOCH(CH3)2
HO
OH
Q6
HO
HO
the molecule are responsible for each signal in its 13C NMR spectrum.
OH
OH
The precise order of carbons within the group of two and the group of three are not required.
200
180
160
140
120
100
/ ppm
80
60
40
20
0
[3]
Q7
Atenolol is an example of the type of medicine called a beta blocker. These medicines
are used to lower blood pressure by slowing the heart rate. The structure of atenolol is shown below.
OH
H2N
CH2
The
CH
CH2
CH3
CH
Q7 (a)
CH2
CH3
q
13
Use the structure of atenolol given to deduce the total number of peaks in the
13
Q7 (b)
Part of the
13
Q7 (c)
13
100
80
60
40
/ ppm
Q7 (d)
There are three CH2 groups in the structure of atenolol. One of these CH2 groups
produces the peak at = 71 in the
13
Draw a circle around this CH2 group in the structure of atenolol shown below.
OH
H2N
C
O
CH2
CH2
CH
CH2
CH3
CH
CH3
[1]
20
Q8
Many aromatic nitro compounds are used as explosives. One of the most famous is
2-methyl-1,3,5-trinitrobenzene, originally called trinitrotoluene or TNT, shown below .
CH3
O2N
NO2
NO2
Q8 (a) Deduce the number of peaks in the 13C n.m.r. spectrum of TNT.
[1]
Q8 (b)
Q8 (c)
Using the molecular formula (C7H5N3O6), write an equation for the decomposition
reaction that occurs on the detonation of TNT. In this reaction equal numbers of moles
of carbon and carbon monoxide are formed together with water and nitrogen.
[1]
Q9
H 2C
CH2
N
H 2C
CH2
H 2C
CH3
H 3C
Q9 (a)
13C
Q9 (b)
absorption
of energy
11
10
/ ppm
3
1
2
Q10
Atenolol is an example of the type of medicine called a beta blocker. These medicines
are used to lower blood pressure by slowing the heart rate. The structure of atenolol is shown below.
OH
H2N
C
O
CH2
CH2
CH
CH2
CH3
CH
CH3
q
Q11
[2]
C
D
A
[1]
Q11 (b)
[1]
Q11 (c)
[1]
Q12
B
C
[1]
Q12 (b)
[1]
Q13
Haloalkanes have been used as aerosol propellants and refrigerants but are now
largely banned due to the damage they cause to the ozone layer.
Halon 1211 was once commonly used in fire extinguishers (now only found in fighter
jets) and Halothane is an inhalational general anaesthetic.
Further examples of haloalkanes are given in the table below.
Common name
Structural
Number of different
formula
fluorine environments
CFC-113
Cl2FC-CClF2
CFC-113a
Cl3C-CF3
HFC-134a
F3C-CH2F
CCl3F
CCl2F2
CFC-13
CClF3
Halon 1211
CBrClF2
Complete the table above indicating the number of different fluorine environments for
each of the compounds AG
Q13 (b)
[3]
The anaesthetic Halothane has the formula C2HBrClF3 and shows one signal in its
19
F NMR spectrum. Draw the two possible three-dimensional structures for Halothane.
[2]
Q13 (c)
[2]
Q13 (d)
[2]
Q14
On the structure of ibuprofen below, mark the protons responsible for the peaks A, B,
C, D, E and F on the spectrum. The integrals and expansions for each peak are shown on the spectrum.
O
CH3
OH
CH3
H3C
[6]
H
R
C
H
1H
2H
H
2H
C
H
2H
1H
2H
Q15
H
C
H
H
O
C
O
C
H
H
C
H
isomer 1
Q15 (a)
H
C
H
H
C
H
isomer 2
Q15 (b)
Q15 (c)
Q15 (d)
integration
10
3
2
5
/ ppm
[6]
Q16
11
10
6
1H
200
180
160
140
NMR spectrum of T
120
13C
100
80
NMR spectrum of T
60
40
20
0
/ ppm
0
/ ppm
[7]
Q17
A, B and C are three structural isomers of molecular formula C6H10O. They are all cyclic.
Isomers A and B have strong infra-red absorptions, A at 1720 cm1 and B at 1780 cm1;
C has an absorption at 1650 cm1 and a broad absorption between 3230 and 3550 cm1.
In the proton n.m.r. spectrum, A has three peaks (signals) with areas in the ratio
2:2:1 whereas B has two peaks in the ratio 3:2; C has 4 peaks with areas in the ratio 1:2:3:4.
[10]