CHAPTER 11 REVIEW Pearson Chemistry 12 Queensland

1 B. The base peak in a mass spectrum corresponds to the strongest signal, and therefore arises from the most
commonly detected fragment. The peak corresponding to the unfragmented molecule is called the molecular ion (or
parent ion) peak.
2 A. Proteins are stained with coomassie blue dye, which is visible as blue bands.
3 C. Reducing the pressure of the mobile phase will decrease the movement of the molecules through the column and
therefore increase the time spent in the column.
4 a the attraction of one substance to another
b a set of techniques used to separate and analyse the components in a mixture
c the breaking of the bonds between a substance and the surface to which the substance is adsorbed
d a liquid used as the mobile phase in chromatography
e the phase that moves over the stationary phase in chromatography
f the solid phase over which the mobile phase moves, allowing the various components of the mixture to be
adsorbed/desorbed at different rates to allow separation
g the time taken for a component to pass through a chromatography column
5 a broad absorption at 3200–3550 cm−1
b absorption at 3500 cm−1 and 1700–1750 cm−1
c absorption at 1670–1750 cm−1
d absorption at 600–800 cm−1
6 Crystals must be perfect (no cracks or flaws) and small enough to allow photons from X-rays to interact with atoms.
7 a mass spectroscopy
b infrared spectroscopy
c mass spectroscopy
8 Step Number

As time progresses during the experiment, smaller fragments move faster and further through the gel than larger 6
fragments. This sorts the fragments by size.

Each protein sample is loaded separately into one of the wells within the gel. A standard protein mixture (called a 4
protein ladder) is also run on the gel for comparison with the samples.

A buffer solution is added to the electrophoresis chamber, covering the gel uniformly. 3

A power source is attached to the electrophoresis bath and switched on. The electrical current causes the negatively 5
charged DNA fragments to migrate through the gel towards the positive terminal of the chamber.

The protein fragments are detected by applying coomassie blue dye that binds to protein. 7

The gel is placed into a gel electrophoresis chamber, with the wells situated at the negative terminal of the chamber. 2

An electrophoresis gel is prepared. It has a jelly-like texture and is usually composed of polyacrylamide gels. The gel 1
is rectangular in shape and contains small wells (holes) at one end.

9 C. Compound B is likely to move more slowly through the column than compound A because it is more strongly
absorbed. Since compound C is least strongly adsorbed on the stationary phase and most soluble in the mobile
phase, it should pass through the column most rapidly.
10 B. Peak area is the true measure of quantity; however, peak height can give a reasonable estimate provided the peaks
are very sharp.
11 D. C–Cl has a higher wavenumber than C–Br and hence requires more energy to vibrate
12 D
13 C−Br, C−O, C−H, O−H
14 Molecular ion has a mass-to-charge ratio (m/z) of 44, and is C3H8+; base ion has a mass-to-charge ratio (m/z) of 29,
15 less than the molecular ion and is C2H5+.
15 The computer could look for specific ion peaks that would correspond to the molecular ions of illegal substances.
It could then confirm the presence of these compounds by identifying the fragment ions of that compound.

Copyright © Pearson Australia 2019 (a division of Pearson Australia Group Pty Ltd) ISBN 978 1 4886 1956 4
 Pearson Chemistry 12 Queensland
16 IR spectroscopy is usually used to identify general functional groups in a molecule but can also be used for positive
identification by analysing the fingerprint region compared to a reference.
Mass spectrometry gives information about the molecular mass and possible fragments within a molecule, which can
lead to confirmation of a suspected structure.
Protein gel electrophoresis can be used to separate and purify protein mixtures for further analysis but can also be
used for positive identification by comparing with known proteins.
X-ray crystallography is used to determine the distances between the nuclei and the angles of atomic and molecular
structures in a crystal of organic material.
17 propanal; the strong sharp absorption at 1750 cm−1 indicates a C=O bond.
18 a Calculate individual polypeptides in each sample:
Sample A: Sample B: Sample C:
(100 × 120)/1000 = 12 kDA (200 × 120)/1000 = 24 kDa (100 × 120)/1000 = 12 kDa
(175 × 120)/1000 = 21 kDa (250 × 120)/1000 = 30 kDa (150 × 120)/1000 = 18 kDa
(250 × 120)/1000 = 30 kDa (350 × 120)/1000 = 42 kDa (175 × 120)/1000 = 21 kDa
(300 × 120)/1000 = 36 kDa (250 × 120)/1000 = 30 kDa
(300 × 120)/1000 = 36 kDa
b A B C
kDa

50

45
42
40

35 36

30 30

25
24
20 21
18
15
12
10

c Drug samples from A and C are similar because they share a large number of bands.
d No, many proteins have the same molecular mass but a different sequence of amino acids.
19 a C6H13NO2
b 131 g mol−1
c OH CH3
15
57
C CH 29 CH3
* *
O CH CH2

16
NH2

d i CH3+
ii C2H5+
iii C4H9+
e i The base peak is the strongest signal in the mass spectrum that is the most abundant fragment ion.
ii 131 − 86 = 45 mass units lost. This is most likely to be CO2H.
20 C4H6. The molecular ion has a mass-to-charge ratio (m/z) of 54 which indicates a molecular mass of 54 g mol−1.
21 Compared with conventional column chromatography, HPLC is more sensitive, faster, resolves components better
and is able to detect colourless components readily.

Copyright © Pearson Australia 2019 (a division of Pearson Australia Group Pty Ltd) ISBN 978 1 4886 1956 4
 Pearson Chemistry 12 Queensland
22 a
14

12

10
Peak area × 104

8
wine sample
6

2.0 4.0 6.0 8.0 10.0 12.0 14.0 16.0

Ethanol content (%)
b 10.4%
c Techniques such as HPLC spectroscopy do not directly produce measures of concentration. Standards must be
used. More than one standard should be used and the unknown sample should lie between these standards. This is
because a zero standard may be contaminated with trace amounts of the chemical being tested. Calibration graphs
are often non-linear and multiple standards increase the chance of detecting incorrectly prepared solutions.
23 a Sample A is a patient who is dehydrated and has an iron deficiency.
Sample B is a patient who has an iron deficiency and a kidney disease.
b Yes, the other proteins can be identified by comparing them to the protein ladder.
24 a C4H10
b C3H6O
c C2H6N2
25 a i 98 corresponds to the molecular ion made up of two 35Cl isotopes
ii 100 corresponds to the molecular ion with one 35Cl and one 37Cl isotope
iii 102 corresponds to the molecular ion with two 37Cl isotopes
b The most abundant Cl isotope is 35Cl; therefore it has a higher peak.
ClCCH3+
c
26 a Both spectra contain broad, strong absorption bands at 3300 cm−1, which corresponds to the expected absorbance
by alcohol O−H bonds. The spectra do not contain peaks at 1700 cm−1 and so they cannot be acids.
b The two spectra have different peaks in the fingerprint region and so cannot be of the same molecule.
27 The mass spectrum shows a molecular ion with a mass-to-charge ratio (m/z) of 88, meaning that the molecular
formula is twice the empirical formula: C4H8O2. The base peak at m/z = 43 could be ion fragments CH3CH2CH2+ or
CH3CO+. The fragment ion at m/z = 29 could be CH3CH2+ or CHO+.
The IR spectrum shows strong absorption bands at 1700 cm−1 and 3000 cm−1, suggesting the presence of acid
hydroxyl and carbonyl groups. The compound is likely to be a carboxylic acid.
The possible semistructural formula for this compound could be CH3CH2CH2COOH and named butanoic acid, or
(CH3)2CHCOOH and named 2-methylpropanoic acid.
28 a Spectrum A: ~ 3000 cm−1 is C−H, ~ 3400 cm−1 is O−H
Spectrum B: ~ 3000 cm−1 is C−H, ~ 1700 cm−1 is C=O
b spectrum A is propan-2-ol; spectrum B is propanone
29 a 58
b It provides the molecular mass from which the molecular formula can be deduced.
c [CH3CO]+
30 a taurine, glycine and an unknown amino acid
b viewing under UV light or applying a stain
distance the greenspot travelled fromorigin 6
c Rf = = = 0.12
distance the solvent front traveles fromorigin 50

d Taurine is bonded least strongly. Strong interactions with the mobile phase will favour desorption and result in
higher Rf values since molecules will spend less time adsorbed to the stationary phase. Taurine has the lowest Rf
value and so does not desorb readily into the mobile phase.

Copyright © Pearson Australia 2019 (a division of Pearson Australia Group Pty Ltd) ISBN 978 1 4886 1956 4
 Pearson Chemistry 12 Queensland
31 Shapes of crystals are due to the regular array of the molecule or atoms. The shape depends on the bonding
interactions between atoms and molecules. The shape of the crystals would only be different if the conditions
influenced the bonding interactions.
32 a Ethyl methanoate is an ester and has the functional group COO. An ester will have a C=O band at around
1670–1750 cm−1; the broad O−H band at 3500 cm−1 from the alcohol will be absent.
b The IR for the carboxylic acid will show a broad O−H band and a C=O band. The alcohol would only show a broad
O−H band.
c Yes, a pure sample of ethyl methanoate can be run and the fingerprint regions compared.
33 a Sorbic acid absorbs most strongly. Its longer retention time indicates that it spends a relatively long time adsorbed
onto the stationary phase.
b Only benzoic acid, for which there is a peak in the sample spectrum with the same retention time. There are no
peaks in the sample with retention times corresponding to the other two.
34 a
9.0

8.0

7.0 line of best fit

6.0
Peak area (cm2)

5.0

4.0

3.0

2.0

1.0 13 ppm

10 20 30
Concentration of insecticide (ppm)

Concentration of insecticide = 13 ppm

b No, the reservoir water is not safe to drink. The 13 ppm concentration of the insecticide is greater than the 10 ppm
health limit.
c Water used for preparing the standards may have been contaminated with insecticide. The injection port of the
column may have been contaminated with insecticide. Small quantities of a substance with a similar retention time
to the insecticide may be present.
35 X-rays are shone onto a crystal of the compounds. The X-rays are diffracted by high-electron density areas in the
molecule, which produces a diffraction map of the molecule. The diffraction map is then analysed and interpreted by
computer analysis which reveals the bond lengths and angles within the structure.
36 a Propanoic acid would have a C=O band at around 1700 cm−1. There would be a difference in the band position for
the O−H group, with the O−H alcohol in the range of 3400–3650 cm−1 and the O−H carboxylic acid band would be
at around 2500–3100 cm−1.
b The O−H alcohol band would be in the same position, but will have different fingerprint regions.
c Propene would have a C=C band at approximately 1700 cm−1.
37 a Number of components and absorbance of components, from which concentration can be determined.
b four
c Solid samples are dissolved in a suitable solvent. The liquid sample is injected into the top of an HPLC column.
The stationary and mobile phases are chosen to achieve a good separation of the components in the sample. The
sample components alternately adsorb onto the stationary phase and then desorb into the solvent as they are
swept forward. The time taken to exit the column increases if the component strongly absorbs onto the stationary
phase and has a low solubility in the mobile phase.

Copyright © Pearson Australia 2019 (a division of Pearson Australia Group Pty Ltd) ISBN 978 1 4886 1956 4