Analytical Chemistry

The NMR spectrum of cysteine, H2NCH(CH2SH)CO2H, shows five absorptions.

After shaking a solution of cysteine with a few drops of D2O, the NMR spectrum shows only
two absorptions, E and F, shown below. 9701/41/O/N/15/Q9/Part d

(i) Identify the two types of protons responsible for the absorptions E and F.
E ..........................................................................................................................................
F...........................................................................................................................................
[1]
(ii) State and explain the splitting patterns of the absorptions E and F.
E ..........................................................................................................................................
..............................................................................................................................................
F ..........................................................................................................................................
........................................................................................................................................ [2]

(a) A mixture of volatile organic compounds X, Y and Z can be separated in a gas chromatograph.
9701/43/O/N/15/Q8

Their identities can be confirmed by measuring their different retention times and comparing to
known values.
A gas chromatogram is shown.
(i) Suggest what is meant by the term retention time.
..............................................................................................................................................
........................................................................................................................................ [1]
(ii) Give an example of a carrier gas used in gas chromatography.
........................................................................................................................................ [1]
(iii) Z spends the longest time in the chromatography column.
Suggest why this might be the case.
..............................................................................................................................................
........................................................................................................................................ [1]
(iv) Explain a possible limitation of gas / liquid chromatography in separating two esters such
as ethyl methanoate, HCO2CH2CH3, and methyl ethanoate, CH3CO2CH3.
..............................................................................................................................................
........................................................................................................................................ [1]
(v) A student works out the areas underneath the three peaks in the chromatogram.

Assuming the areas underneath the peaks are proportional to the masses of the respective
components, what percentage of the original mixture was made up of the organic
compound, X?
% of X = ........................ [1]

(b) The NMR spectrum of Y given below shows four absorptions.

(i) What compound is responsible for the absorption at δ = 0?
........................................................................................................................................ [1]
(ii) Compound Y is an ester with the molecular formula C4H8O2.
Complete the table for the NMR spectrum of Y.
The actual chemical shifts for three absorptions in Y and the splitting pattern for the
resonance at δ = 3.7 ppm have been given for you.
Use of the Data Booklet may be helpful.

(iii) Use your conclusions to suggest a structure for the ester Y.

[1]
[Total: 11]
1.(a) NMR spectroscopy and X-ray crystallography can both be used to examine the structure of
organic compounds. 9701/42/M/J/15/Q8

NMR is very useful at examining hydrogen atoms in compounds, but hydrogen atoms are
invisible to X-rays.
(i) Explain why NMR spectroscopy can detect hydrogen atoms in molecules.
.............................................................................................................................................
....................................................................................................................................... [1]
(ii) Explain why hydrogen atoms are invisible to X-rays.
.............................................................................................................................................
....................................................................................................................................... [1]
(iii) The molecular formula of the amino acid cysteine is C3H7O2NS.
Explain which of the atoms present would show the greatest absorption on exposure to
X-rays.
.............................................................................................................................................
....................................................................................................................................... [1]
(b) The NMR spectrum below was obtained from an organic liquid, P, which contains fi ve carbon
(i) How many protons are present in one molecule of P? Explain your answer.
number of protons ............................
.............................................................................................................................................
....................................................................................................................................... [1]

(ii) When a little D2O is added to P, the absorption at δ 2.0 disappears.

Explain what this tells you about the group responsible for this absorption and why.
.............................................................................................................................................
.............................................................................................................................................
....................................................................................................................................... [2]
(iii) What does the absorption at δ 0.9 tell you about the adjacent carbon atom?
.............................................................................................................................................
....................................................................................................................................... [1]
(iv) What group(s) is/are responsible for the absorption at δ 0.9?
....................................................................................................................................... [1]
(v) Suggest a structure for P.
[1]
(c) When an isomer of P is heated with concentrated H2SO4 it forms a new compound, Q. This new
compound Q reacts with bromine to give a dibromide, R.
(i) A mass spectrum was obtained of R. The ratio of the heights of the M : M+1 peaks
was 9.3 : 0.5.
Show that there are fi ve carbon atoms present in one molecule of R.
[1]
(ii) Predict the ratio of the heights of the M : M+2 : M+4 peaks as a result of the two bromine
atoms in the dibromide R. Show your working.
ratio ...................................... [1]
(iii) What is the molecular formula of R?
....................................................................................................................................... [1]
[Total: 12]

(a) (i) The nucleus / proton of a hydrogen atom has spin [1]
(ii) Hydrogen doesn't have enough electrons / electron density [1]
(iii) S / sulfur – it has the greatest number of electrons or highest electron density [1]
(b) (i) 12 protons (=9+2+1) [1]
(ii) The group responsible for this peak is –OH (allow NH) [2]
The D in D2O exchanges with the H in –OH or H is replaced by D
or "–OH → –OD",
(iii) The adjacent carbon atom has no hydrogen atoms bonded to it [1]
(iv) Methyl / CH3 group [1]
(v) P is (CH3)3C–CH2OH [1]

(a) A chemist analysed a mixture and separated compound Y using gas chromatography (GC), and
measured its retention time. 9701/04/SP/16/Q9
State what is meant by retention time.
..................................................................................................................................................
.............................................................................................................................................. [1]
(b) Compound Y was analysed using two techniques with the following results.
The mass spectrum showed that,
• the M peak was at m/e 86,
• the ratio of heights of the M and M+1 peaks was 23.5 : 1.3.
(i) Use these data about the ratio of peak heights to show that there are fi ve carbons in Y.
[1]
(ii) Use this spectrum to describe the main features of Y. Use of the Data Booklet may be
helpful.
...........................................................................................................................................
...........................................................................................................................................
...................................................................................................................................... [3]

(iii) Y is one of three isomeric ketones R, S or T.

Use the carbon-13 NMR spectrum to identify Y as either R, S or T.

Explain how you ruled out the other two isomers.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...................................................................................................................................... [3]
[Total: 8]
The combination of mass spectroscopy and NMR spectroscopy provides a powerful method of
analysis for organic compounds. 9701/41/M/J/14/Q7

(a) The mass spectrum of a compound G contains M and M+1 peaks in the ratio of their heights
of 74 : 2.5.
Use these data to calculate the number of carbon atoms present in G. Show your working.
[2]
(b) The NMR spectrum of compound G is shown.
(i) Use the Data Booklet and your knowledge of NMR spectroscopy to identify the type of
proton responsible for each of the three absorptions.

(ii) The addition of D2O causes one of these absorptions to disappear.

Explain why this happens and state which absorption is affected.
.............................................................................................................................................
.............................................................................................................................................

(iii) Draw the structural formula of G.

[6]
(c) Several structural isomers of G exist.
(i) Draw the structural formula of an isomer of G with only two absorptions in its NMR
spectrum.
(ii) Use the Data Booklet to suggest where these absorptions would occur.
Q. T is a saturated alcohol. It was analysed by mass spectroscopy and NMR spectroscopy.
In the mass spectrum, the molecular ion peak, M, was at an m/e value of 74 and the ratio of the
heights of the M and M+1 peaks was 20.4 : 0.9. 9701/41/O/N/14/Q8

(a) (i) Use the ratio of the heights of the M and M+1 peaks to calculate the number of carbon
atoms in a molecule of T.
(ii) What is the molecular formula of T?
molecular formula = .....................................
[3]
(b) The NMR spectrum of T given below shows four absorptions. The absorption at 1.8 ppm is a
multiplet and that at 2.5 ppm is a singlet.
(i) Use this information and your answer to (a)(ii) to deduce the structure of T.

(ii) Describe and explain which type of proton is responsible for each of the absorptions.
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
(iii) The absorption at 1.8 ppm is a multiplet and that at 2.5 is a singlet.
State and explain the splitting patterns of the other absorptions, at 0.9 and 3.4 ppm.
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
(iv) Describe and explain how the NMR spectrum of T dissolved in D2O would differ from the
one shown.
.............................................................................................................................................
.............................................................................................................................................
.............................................................................................................................................
[9]
[Total: 12]

Q. (a) Explain what is meant by the term partition coeffi cient. 9701/43/O/N/14/Q7
....................................................................................................................................................
.............................................................................................................................................. [2]
(b) When 20 cm3 of ethoxyethane were shaken with 75 cm3 of an aqueous solution containing
5.00 g of an organic compound, J, in 75 cm3 of water, it was found that 2.14 g of J were extracted
into the ethoxyethane.
Calculate the partition coeffi cient, Kpartition, of J between ethoxyethane and water.
Kpartition = ...................... [2]
(c) In a new experiment
● 10 cm3 of ethoxyethane were shaken with 75 cm3 of an aqueous solution containing 5.00 g
of J and the layers were separated.
● The aqueous layer was shaken with a second 10 cm3 portion of ethoxyethane and the
layers were separated.
● The two organic layers were combined.
Use the value of Kpartition you calculated in (b) to calculate the total mass of J extracted by this
procedure.
total mass of J = ...................... [2]
(d) Paper chromatography and gas / liquid chromatography both rely on the partition of compounds
between mobile and stationary phases.
(i) Identify the mobile phase in paper chromatography.
.............................................................................................................................................
(ii) Suggest what type of liquid is used for the stationary phase in gas / liquid chromatography.
.............................................................................................................................................

(iii) Both these techniques can be used to separate mixtures.

State what you would measure in order to distinguish between the components in the mixture
in
1. paper chromatography, ..................................................................................................
2. gas / liquid chromatography. ...........................................................................................

[4]
(e) A mixture of three compounds was analysed by paper chromatography using a non-polar
solvent. The resulting chromatogram is shown.

Identify which compound is responsible for each spot.

Q. The techniques of mass spectrometry and NMR spectroscopy are useful in determining
the structures of organic compounds. 9701/42/M/J/13/Q7

(a) The three peaks of highest mass in the mass spectrum of organic compound L
correspond to masses of 142, 143 and 144.
The ratio of the heights of the M : M+1 peaks is 43.3 : 3.35, and the ratio of heights of
the M : M+2 peaks is 43.3 : 14.1.

(i) Use the data to calculate the number of carbon atoms present in L.

(ii) Explain what element is indicated by the M+2 peak.

....................................................................................................................................
....................................................................................................................................
Compound L reacts with sodium metal. The NMR spectrum of compound L is given
below.
(iii) What does the NMR spectrum tell you about the number of protons in L and their
chemical environments?
....................................................................................................................................
....................................................................................................................................

(iv) Use the information given and your answers to (i), (ii) and (iii) to deduce a structure
for L.
Explain how you arrive at your answer.
(b) The molecular formula C3H6 represents the compounds propene and cyclopropane.

(i) Suggest one difference in the fragmentation patterns of the mass spectra of these
compounds.
....................................................................................................................................
....................................................................................................................................
(ii) Suggest two differences in the NMR spectra of these compounds.
....................................................................................................................................
....................................................................................................................................
....................................................................................................................................
[3]
[Total: 10]
Q. Instrumental analysis plays an increasingly important role in modern chemistry. Two
important techniques are NMR spectroscopy and X-ray crystallography. 9701/43/O/N/13/Q8

(a) Both techniques use part of the electromagnetic spectrum.

Which technique uses radiation with the longer wavelength, and in which part of the
spectrum is it found?
...........................................................................................................................................
[1]
(b) NMR spectroscopy provides detailed information about protons, but X-ray crystallography
is unable to detect them. Explain these facts.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
[2]
(c) The protein found in hair contains the amino acid cysteine, C3H7SNO2. Crystalline
cysteine was examined using X-ray crystallography. State which atom produced the
strongest refl ection, explaining your answer.
...........................................................................................................................................
...........................................................................................................................................
[1]
(d) Compound P is an alcohol that can be converted into compound Q in the following
reaction sequence.

P → CxH6O → Q
Spectral analyses of P and Q were carried out.
(i) The mass spectrum of P shows an M : M+1 peak ratio of 4.5 : 0.15.
Calculate the number of carbon atoms in P.

The NMR spectra of P and Q are shown below.

(ii) In the spectrum of P, clearly label the peak due to the –OH group with an X.
(iii) State how many different proton environments are present in compound Q.
......................................
(iv) What evidence is there in these spectra that P is a primary rather than a secondary
alcohol?
....................................................................................................................................
....................................................................................................................................
....................................................................................................................................
(v) Draw a structure for Q.
[6]
[Total: 10]
(a) NMR and radiowaves (or VHF / UHF or 40 – 800 MHz) [1]
[1]
(b) NMR: protons have (nuclear) spin
or (spinning) proton produces magnetic moment / field or two spin states
or protons can align with or against an applied magnetic field [1]
there is insufficient electron density / cloud around H atoms for X-ray crystallography [1]
[2]
(c) Sulfur, because it has the highest electron density [1]
[1]

(iv) Q has peak at 11.7δ. [1]

which is due to –CO2H [1]
(This can only be formed by oxidising a primary alcohol.)
or P has 4 peaks in its NMR spectrum, not 3 [1]
in a secondary alcohol with 3 carbons, two (methyl) groups will be in the same
chemical environment (or wtte) [1]
or analysis of the splitting pattern in P: the peaks at δ 0.9 and 3.6 are triplets, [1]
so each must be adjacent to a –CH2– group. (hence –CH2–CH2–CH3) [1]
(v) CH3CH2CO2H (structure needed, not name) [1]
[6]
[Total: 10]

Q. another form, buckminsterfullerene, was discovered, in which the carbon exists as

spherical molecules. 9701/43/O/N/13/Q9

(a) The other two forms of carbon have very different structures.
(i) Name these two forms.
.............................................................. and ..............................................................
(ii) Give three differences in physical properties between these two forms.
....................................................................................................................................
....................................................................................................................................
....................................................................................................................................
[4]

(b) The diagram shows the structure of buckminsterfullerene.

The molecule of buckminsterfullerene contains 60 carbon atoms. Suggest a reason why
buckminsterfullerene reacts with hydrogen under suitable conditions and give a formula
for the product.
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
[2]

(c) In 2010, two scientists from the University of Manchester were awarded the Nobel Prize
for Physics for their work on graphene, a new structural form of carbon. Graphene
is one of the new ‘nano-materials’ being developed for commercial uses in the next
10 years.

(i) Graphene is in the form of sheets of carbon one atom thick. Calculate the number
of carbon atoms present in a sheet of graphene with a mass of one thousandth of a
gram (0.001 g).
The number of hexagons in a large sheet of graphene can be assumed to be one half of
the number of carbon atoms. Each hexagon has an area of 690 nm2.
(ii) Calculate the area of the sheet of graphene in (i).
area of sheet = .......................... nm2
(iii) Would you expect samples of graphene and buckminsterfullerene to be electrical
conductors? Explain your answers.
graphene ...................................................................................................................
....................................................................................................................................
buckminsterfullerene .................................................................................................
....................................................................................................................................
[4]
[Total: 10]
Q. A sample of a liquid, P, was found at the scene of the crime and was analysed using
mass spectrometry and NMR spectroscopy. 9701/41/O/N/12/Q7 part c

The mass spectrum has M and M+1 peaks in the ratio of 5.1: 0.22 with the M peak at
m/e = 88.
The NMR spectrum is shown

Use the data to suggest a structure for P, explaining your answer.

...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
...........................................................................................................................................
structure of P
[5]
Q. Although the chemical reactions of compounds remain important pointers to their
functional groups, instrumental techniques such as mass spectrometry and NMR spectroscopy
are increasingly used to determine molecular structures. 9701/43/O/N/12/Q7

(a) Compound J was analysed using these two techniques with the following results.
The mass spectrum showed that
● the M peak was at m/e 86,
● the ratio of heights of the M and M+1 peaks was 23.5 : 1.3.
The NMR spectrum is shown below.

(i) Use the data to determine the number of carbon and hydrogen atoms present in J,
showing your working.
(ii) Use the information given above and your answer to (i) to identify the other element
present in J.
........................................................................
(iii) Determine the structure of J, explaining how you reach your conclusion.
structure of J
explanation ................................................................................................................
....................................................................................................................................
[5]

In paper chromatography, better separation may be achieved by running the chromatogram

in one solvent, then turning the paper at right angles and running it in a second
solvent. The chromatogram below was produced in this way.

(b) Chromatography is another important analytical technique used in chemistry.

(i) Paper, thin-layer and gas-liquid chromatography rely on different physical methods to
separate the components in a mixture. Complete the table indicating the appropriate
method on which the technique is based.
(ii) How many spots were visible before solvent 2 was used?
..................................
(iii) Ring the spot that did not move in solvent 2.
(iv) How many spots travelled further in solvent 2 than they did in solvent 1?
..................................
[5]
[Total: 10]
Q. (c) Propene was treated with bromine in the presence of chloride ions and the product
analysed using mass spectrometry. 9701/41/M/J/12/Q7 part c

A group of peaks was found in the range m/e 156–160 with the following relative heights

(i) Identify the species responsible for each of these peaks.

156 .............................................................................................................................
158 .............................................................................................................................
160 .............................................................................................................................
A large peak was present in the spectrum with a m/e value of less than 20.
(ii) Suggest the m/e value for the peak and the species that produced it.
m/e .......................................................
species .................................................
[4]
Q. study the structure and function of molecules.
(a) Nuclear magnetic resonance, NMR, arises because protons possess spin which
generates a small magnetic moment. When an external magnetic fi eld is applied the
protons can align with or against the external fi eld. If they are given a small amount
of energy in the radio frequency range each can be ‘promoted’ so that their magnetic
moment opposes the external fi eld.
Two factors can infl uence the energy required for this promotion. What are they?
(i) ....................................................................................................................................
(ii) ....................................................................................................................................
[2]
(b) A compound, J, has the formula C4H10O. The NMR spectrum of J is shown.
(i) Indicate the groups responsible for each peak and hence deduce the structure of J.
peak at 1.26 δ ................................. peak at 2.0 δ .................................
structure of J

(ii) There are three other isomers of J containing the same functional group as J.
Draw the structures of two of these three isomers and indicate how many different
chemical shifts each would show in its NMR spectrum.
isomer 1 isomer 2
number of groups of peaks .................... number of groups of peaks ....................
[6]
(c) X-ray crystallography can be useful in gathering information about the structure of large
organic molecules, such as nucleic acids.
(i) Which element will show up most strongly in the X-ray crystallography of a nucleic
acid? Explain your answer.
....................................................................................................................................
....................................................................................................................................
(ii) X-ray crystallography will not detect hydrogen atoms. Explain why this is so.
....................................................................................................................................
....................................................................................................................................
[2]
[Total: 10]

(a) (i) + (ii) any two from:

• The nature/electronegativity of the atom the proton is attached to or is near or the
electronic/chemical environment of the proton
• The number/spin states of adjacent protons or protons attached to adjacent atoms
• The (strength of) the applied/external magnetic field [1] + [1]
[2]
(b) (i) Peak at 1.26δ = (3 ×) CH3 or methyl and Peak at 2.0δ = –O–H or alcohol [1]

(c) (i) Phosphorus – it has more electrons or high electron density (NOT phosphate) [1]
(ii) H atoms don’t have enough electron density to show up or they only contain one e– [1]
[2]
[Total: 10]

Q. The developments in nanotechnology and drug delivery over the past 20 years have been
wide-ranging. 9701/42/M/J/12/Q8

(a) One of the most widespread developments for delivering a range of pharmaceutical
products has been the use of liposomes. These are artifi cially created spheres made
from phospholipids which have an ionic phosphate ‘head’ and two hydrocarbon ‘tails’.

Liposomes have also been used to carry pharmaceuticals such as vitamins and moisturisers used
in cosmetic anti-ageing creams. Otherwise these pharmaceuticals

may be oxidised or dehydrated if exposed to air.

(i) State in which area of the liposome, A, B or C, each of the following types of molecule
would be carried.
a hydrophilic moisturiser ..............................
a fat-soluble vitamin ..............................
(ii) For one of the areas, A, B or C, suggest why this would not be an appropriate place
to carry either molecule.
....................................................................................................................................
....................................................................................................................................
....................................................................................................................................
[3]
(b) When liposomes are used to carry drugs, their main purpose is to prevent the drug
molecules from being broken down on passage through the digestive system.
(i) Name a functional group present in drug molecules that might be broken down by
acid in the stomach.
....................................................................................................................................

(ii) Name the type of reaction that would cause such a breakdown.
....................................................................................................................................
(iii) The drug Sirolimus is used to suppress possible rejection by the body after kidney
transplants.

Circle two bonds, each in a different functional group that could be broken down in
the digestive system.
[4]
(c) Sirolimus is not very soluble in water, greatly reducing its effectiveness when given by
mouth or by injection. To increase its effectiveness when taken by mouth nano-sized
crystals of the drug combined with poly(ethylene glycol) or PEG (shown below) are
produced.
HO — (CH2 — CH2 — O)n — H
(i) Suggest what is meant by the term nano-sized.
....................................................................................................................................
(ii) Suggest where on the molecule of PEG the drug would be attached.
....................................................................................................................................
(iii) Why would bonding the drug to a PEG molecule improve its solubility in water?
....................................................................................................................................
[3]
[Total: 10]

(a) (i) hydrophilic in area C [1]

fat-soluble in area B [1]
(ii) A – region would be exposed to the atmosphere/water/enzymes or nothing the molecule
can attach to at A [1]
[3]
(b) (i) amide/peptide or ester [1]
(ii) hydrolysis [1]

(c) (i) measured in nm, i.e. between 1 and 1000 nm (or 10–9 – 10–6
m). Any quoted value
or range between these limits is acceptable [1]
(ii) One or both of the –OH groups (NOT just ‘oxygen’ or ‘O’) [1]
(iii) PEG can H-bond (with water) because it is hydrophilic/contains an OH group/contains
lots of oxygen atoms [1]
[3]
[Total: 10]
Q. Chromatography is an important analytical technique in chemistry. There is a number of
techniques under the general heading of chromatography. 9701/41/M/J/11/Q8

(a) Paper and gas chromatography rely on partition to separate the components in a
mixture, whereas thin-layer chromatography uses adsorption.
Explain what is meant by (i) partition and (ii) adsorption, in the context of
chromatography.
(i) partition ....................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) adsorption ................................................................................................................
..................................................................................................................................
.............................................................................................................................. [2]
(b) In paper or thin-layer chromatography, better separation may be achieved by running
the chromatogram in one solvent, then turning the paper at right angles and running it in
a second solvent. The chromatogram below was produced in this way.

(i) Ring the spot which was insoluble in solvent 1.

(ii) Label as A and B the spots which were not resolved using solvent 1.
[2]
(c) The mass spectrum shown was obtained from a compound of formula CpHqX, where X
represents a halogen atom.

(i) Deduce the identity of X, giving a reason.

X is ..........................................................................................................................
..................................................................................................................................
(ii) If the relative heights of the M and M+1 peaks are 9 and 0.3 respectively, calculate
the value of p. Use this value and the m / e value of the molecular ion to calculate
the value of q, and hence the molecular formula of the compound. Show your
working.
(iii) Suggest a formula for the ion responsible for the peak labelled R.
....................................................... [4]
(d) In the fragmentation of alcohols which occurs in a mass spectrometer, small stable,
neutral molecules are sometimes produced. Suggest the identity of two such molecules,
each with an Mr less than 30.
(i) ....................................................... (ii) ....................................................... [2]
[Total: 10]

(a) partition – separation due to the different solubilities of compounds in two solvents/phases
[1]
adsorption – separation due to the different attractions between the compounds and the
stationary phase, relative to their solubility in the solvent [1]
Note, if candidates do not refer to different solubilities and different attractions max 1
Q. Enzymes are a special group of protein molecules present in large amounts in living
organisms. Enzymes behave as catalysts but, unlike inorganic catalysts, they generally
catalyse only one particular reaction. 9701/41/M/J/11/Q7

(a) Inorganic catalysts often work better on heating, but enzymes rarely work at temperatures
much above 45°C. Explain why this is the case.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(b) Using the shape below to represent an enzyme, sketch how an enzyme is specific to
the breakdown of a particular substrate molecule enzyme

(c) Describe the effects of a competitive, and of a non-competitive inhibitor on the interaction
between enzyme and substrate.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(d) (i) The diagram shown illustrates an enzyme-catalysed reaction. On the diagram
sketch the graph that would be obtained if the same reaction was carried out in the
presence of a non-competitive inhibitor.
(ii) Explain why a non-competitive inhibitor has this effect on the reaction.
..................................................................................................................................
..................................................................................................................................
[3]
[Total: 10]

(a) The tertiary/3-dimensional structure/shape is held together by hydrogen/ionic/van der Waals

bonds [1]
These break (relatively) easily/are weak/break at/above 45 °C [1]

(c) a competitive inhibitor combines with the enzyme’s active site (so preventing the substrate
from binding) [1]
non-competitive inhibitor bonds with the enzyme away from the active site/at an allosteric site
[1]
this changes the shape of the active site [1]
Also allow competitive inhibition can be overcome by increasing [substrate] or
non-competitive inhibition cannot be removed by increasing [substrate] for the 3rd mark

Line must be of similar shape to original but level out below original line [1]
(ii) Inhibitor reduces the number of enzymes with ‘working’ active sites (owtte) [1]
[Total: 10]

Q. Enzymes are protein molecules that are highly efficient in catalysing specific chemical
reactions in living organisms. 9701/42/M/J/11/Q6

(a) To work in tissues, enzyme molecules generally need to be water-soluble. What does
this tell you about the nature of the side-chains on the exterior of the molecules?
..........................................................................................................................................
...................................................................................................................................... [1]
(b) Enzymes function by a substrate molecule interacting with a particular part of the
enzyme known as the ‘active site’. The substrate is converted into products that are then
released, to be replaced by another substrate molecule.
(i) Describe briefly the primary, secondary and tertiary structures of an enzyme.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) The activity of an enzyme depends upon the tertiary structure of the protein
molecule. Explain how the tertiary structure produces an effective active site.
..................................................................................................................................
..................................................................................................................................
(iii) Give two conditions that can reduce the activity of an enzyme, explaining the
reason in each case.
I ................................................................................................................................
..................................................................................................................................
..................................................................................................................................
II ...............................................................................................................................
..................................................................................................................................
..................................................................................................................................
[6]

(c) An individual enzyme operates best at a specific pH. Different enzymes operate best
under conditions of different pH. Three enzymes involved in the digestion of food are
amylase, pepsin and trypsin.
• Amylase, found in saliva, hydrolyses starch to a mixture of glucose and maltose
under approximately neutral conditions.
• Pepsin hydrolyses proteins to peptides in the acid conditions of the stomach.
• Trypsin continues the hydrolysis of peptides to amino acids in the mildly alkaline
conditions of the small intestine.
The graph below shows the activity of two of the three enzymes mentioned above.

(i) Label each peak shown with the name of the enzyme responsible, either amylase,
pepsin or trypsin.
(ii) On the axes above, sketch the graph that the third enzyme would produce, and
label it with the name of that enzyme.
[3]
[Total: 10]

(a) They are polar/ionic or can hydrogen-bond or are hydrophilic. [1]

(NOT ‘contain the –OH group’, on its own)
[1]
(b) (i) Primary structure is the sequence/order of amino acids [1]
Secondary structure is the H-bonding between C=O & N-H or peptide group/bonds [1]
Tertiary structure gives the (overall) 3D structure/shape/folding/globularity
(not ‘coiling’ on its own)
or mention of at least one method of forming the 3° structure, e.g.; hydrogen bonding
between R-groups/side chains; –S-S- bridges; van der Waals forces; ionic interactions
[1]
(ii) The 3° structure provides a complementary shape to that of the substrate
or it provides the right/specifically shaped cavity for the substrate. (NOT just ‘a cleft’)
or provides nearby groups to aid the reactions of the substrate (owtte) [1]
(iii) Two conditions out of the following:
(a) Increased temperature
(b) Decreased temperature
(c) Change in pH
(d) Addition of heavy metals (or specified, e.g. Hg/Ag)
(e) Addition of inhibitors (competitive or non-competitive)
Suitable reasons:
(i) 3D structure changes shape/is deformed/is broken or R-R interactions (or a specific
example, e.g. H-bonding) are broken
(ii) inhibitor occupies active site.
(iii) either fewer substrate molecules with E > Ea or fewer successful collisions [2]

Q. Nanotechnology is a fast-developing area of science based on the ability to manipulate

materials of very small dimensions. 9701/42/M/J/11/Q8

(a) On the scale shown in metres, mark the upper and lower limits of the range of sizes for
nanoparticles.
(b) One of the most commonly recognised nanoparticles is the ‘buckyball’, a spherical form
of carbon containing 60 carbon atoms. It has been referred to as the third allotrope of
carbon.

Diamond and graphite are two other allotropes of carbon. Suggest what is meant by the
term allotrope.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(c) Nanoparticles are used to deliver drugs within cells. Suggest what property of
nanoparticles enables them to be used in this way. Explain your answer.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]

(d) Copper is an important metal that has been used for thousands of years. The problem
today is that most of the ores rich in copper compounds have been used up. A century
ago ores containing >2% of copper by mass would have been worked; today’s mines
have to operate at much lower percentages, down to 0.5% of copper by mass.
(i) By what type of reaction is the copper present in the ore converted to copper
metal?
......................................................
One of the main ores of copper contains the mineral chalcopyrite, CuFeS2.
(ii) Calculate the percentage of copper by mass in chalcopyrite.
(iii) If the ore contains 2% of chalcopyrite by mass, calculate the mass of copper which
can be produced from each tonne of ore.
(iv) Certain bacteria are able to extract copper from the ‘spoil’ heaps of previously
mined copper ore. These bacteria are sprayed onto the spoil heaps in an aqueous
solution and the resulting solution containing iron(II) sulfate and copper(II) sulfate
is collected in tanks.
Suggest how the copper could be recovered as metal.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 10]

(a) Range should be from 10–6–10–7 (the left hand arrow) [1]
to 10–8–10–9 (the right hand arrow) [1]
[2]
(b) Forms of the same element (or of carbon, since carbon is the context of the question) [1]
with different structures/arrangements of atoms [1]
allow ‘different molecular structure’, but not structural formula. Any mention of ‘compound’
negates the mark.
[2]
(c) Nanoparticles are smaller than (animal) cells or they can pass through the cell membrane
or pass into/between cells [1]
Drugs can be bound to/enclosed by the nanoparticle [1]
[2]
(d) (i) Reduction/redox [1]
(ii) Mr of chalcopyrite is 63.5 + 56 + 64 = 183.5
Mass of copper present is 63.5
Hence percentage of copper present =
183.5
63.5×100
= 34.6% [1]
(if Ar(Cu) = 64 is used, ans = 34.8%. allow 34–35%)
(iii) If the ore contains 2% of chalcopyrite by mass, calculate how much copper is produced
from each tonne of ore.
1 tonne = 1000 kg
1 tonne of chalcopyrite would produce 346 kg of copper
1 tonne of 2 % ore would produce 346 × 0.02 or 6.9 kg of copper ecf from (d)(ii) [1]
(accept 7.0 or 7 kg)
answer may be given as 7000 g or 7 × 10–3 tonnes. If no units are given, assume they
are tonnes, and mark accordingly)
(iv) By displacement with a metal (the following specified metals higher than Cu in the ECS
may be used: Fe, Zn, Sn, Pb, Al, Mg. (NOT Ca, Li, Na. K etc.) or with a suitable nonmetallic
reducing agent, e.g. SO2 or Sn2+, but not something that wouldn’t react, like H2
or By electrolysis (with carefully controlled voltage) [1]
[4]
[Total: 10]
Q. Drugs can be delivered in a number of ways. The method chosen depends both on the
nature of the drug, and the problem it is being used to treat. 9701/43/O/N/11/Q8

(a) Many common drugs are taken by mouth in forms similar to those shown.

(i) Some drugs are available in solution. How would the speed of action of this form
compare with P and Q? Explain your answer.
..................................................................................................................................
..................................................................................................................................
(ii) Explain which of the two forms, P or Q, would act the most rapidly when taken by
mouth.
..................................................................................................................................
..................................................................................................................................
(iii) Some drugs are broken down before they can be absorbed by the intestine. Suggest
how the design of Q prevents this.
..................................................................................................................................
..................................................................................................................................
[3]
(b) After an abdominal operation drugs are often delivered by means of a ‘drip’ inserted
into a blood vessel in the patient’s arm. Explain why this is more effective than taking
painkillers by mouth.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
[2]

(c) One of the molecules that has found a variety of uses in drug delivery is poly(ethylene
glycol) or PEG. It is formed from dihydroxyethane, HOCH2CH2OH.

(i) What type of reaction is this?

..................................................................................................................................

Attaching a PEG molecule to a drug increases the time that it takes for the drug to be
broken down and flushed from the body. There are thought to be two major reasons for
this: firstly the PEG can form bonds to slow the passage of the drug around the body;
secondly it may reduce the efficiency of breakdown of the drug by enzymes.

(ii) What type of bonds would the PEG part of the molecule form with molecules in the
body?
..................................................................................................................................
(iii) Suggest why attaching a PEG molecule to a drug molecule would reduce the rate
of the drug’s decomposition by enzymes.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iv) Drugs are often protein or polypeptide molecules. What type of reaction might occur
in the breakdown of such a drug?
..................................................................................................................................
[5]
[Total: 10]

(a) (i) Soluble form would be most effective [1]

(ii) Q, since the ‘mini-pills’/granules/powder have a larger surface area
or P, because it has no protective casing [1]
(iii) The gel coat stops it being broken down while passing through the upper part of the
digestive system/stomach
or the gel coat is stable to stomach acid. [1]
[3]
(b) The drug is taken quickly/directly to the target
or more accurate dosing can be achieved [1]
When the drug is taken by mouth it has to pass through the stomach/intestine wall to get into
the bloodstream. or some is digested/lost to the system [1]
[2]
(c) (i) condensation (polymerisation) [1]
(ii) hydrogen bonds or van der Waals’ [1]
(iii) It would change the overall shape of the (drug) molecule
The ‘fit’ into the active site would be less effective [1] + [1]
(iv) Hydrolysis [1]
[5]
[Total: 10]

Q. Different analytical techniques are used to build up a picture of complex molecules. Each
technique on its own provides different information about complex molecules but
together the techniques can give valuable structural information. 9701/43/O/N/11/Q7

(a) Complete the table, identifying the technique which can provide the appropriate structural
information.
(b) One general method of separating organic molecules is chromatography. Briefly explain
the chemical principles involved in each of the following techniques.
(i) paper chromatography
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(ii) thin-layer chromatography
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[2]

(c) A combination of mass spectrometry and NMR spectroscopy is often enough to

determine the structure of a simple organic compound.
The organic compound N produced a mass spectrum in which the ratio of the M:M+1
peaks was 5.9:0.20, and which had an M+2 peak of similar height to the M peak.
(i) Calculate how many carbon atoms are present in one molecule of N.
(ii) Deduce which element, other than carbon and hydrogen, is present in N.
................................................................
(iii) Explain how many atoms of this element are present in one molecule of N.
..................................................................................................................................
..................................................................................................................................
The NMR spectrum of N is shown.
(iv) State the empirical formula of N and, using the NMR data, suggest the structural
formula of N, explaining your reasons.
[6]
[Total: 11]
Q. A range of modern analytical techniques has made the identification of molecules, and
atoms in compounds, much more rapid than traditional laboratory analysis. 9701/41/M/J/10/Q9

(a) One instrumental technique is NMR spectroscopy, which uses the fact that under certain
conditions protons can exist in two different energy states.
Explain how these different energy states arise.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(b) When methanol, CH3OH, is examined using NMR spectroscopy, it absorbs at two
different frequencies. Explain why, and predict the relative areas of the two peaks.
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(c) The NMR spectrum below is that of one of three possible isomers of molecular formula
C3H6O2.
The compound could be propanoic acid, methyl ethanoate or ethyl methanoate.
(i) In the boxes provided, draw the structures of the three compounds.

(ii) Explain which compound produced the spectrum shown, indicating which protons
are responsible for each of the peaks A and B.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
(iii) The NMR spectrum of another of the compounds has a peak at 11.0.
State which compound this would be, and identify the proton(s) responsible for this
peak.
compound ..................................................
proton(s) ..................................................
[4]
(d) X-ray crystallography is a technique used to identify the relative positions of atoms in a
crystal of a compound.
(i) What further information about organic macromolecules can be deduced by the
use of X-ray crystallography?
..................................................................................................................................
..................................................................................................................................
(ii) Which atoms cannot be located by X-ray crystallography?
........................................................
[2]
[Total: 10]

(a) spinning proton produces two spin states / magnetic moments (1)
these can align with or against an applied magnetic field (1) [2]
(b) field experienced by protons is influenced by adjacent atoms / protons are in two
different chemical environments (1)
peaks are in the area ratio 3 : 1 (methyl to –OH protons)
or are at 0.5 – 6.0δ and 3.3 – 4.0δ (1) [2]

(ii) compound is CH3CO2CH3 or methyl ethanoate (1)

the other two compounds each have 3 different proton environments, but the
spectrum shows only 2 peaks. (1)
A is OCH3, B is CH3CO (1)
(iii) compound – propanoic acid or ethyl methanoate
the –OH proton or the H–CO proton (1) [6]
(d) (i) distance between atoms / bond lengths / bond angles (1)
(ii) hydrogen atoms (1) [2]
[Total: 12 max 10]
[Total: 10]

Q. The nature and variety of drugs that are available to treat diseases or life-threatening
conditions has never been greater. At the same time, we are much better able to deliver
drugs to their targets in the body.
(a) Some drugs have to be given by injection, rather than by mouth.
Name a functional group in a drug molecule that might be broken down by the acid in
the stomach.
...................................................................................................................................... [1]
(b) The anti-cancer drug Taxol could be broken down if taken by mouth.
Circle two bonds, each in a different functional group, that could be hydrolysed in the
digestive system. [2]

(c) One way of protecting drug molecules that are taken by mouth is to enclose them in
liposomes. These are artificially created spheres made from phospholipids which have
an ionic phosphate ‘head’ and two hydrocarbon ‘tails’.
(i) State in which area of the liposome, A, B or C, each of the following types of drug
would be carried.
a hydrophilic drug .........................
a hydrophobic drug .......................
(ii) For the remaining position, A, B or C, explain why this would not be a suitable area
for carrying a drug.
..................................................................................................................................
..................................................................................................................................
[3]
(d) One way of carrying drugs in the bloodstream is to attach them by a chemical bond to a
polymer. One such polymer is polyethylene glycol or PEG.
HO – (CH2 – CH2 – O)n – H
(i) Where would a drug be attached to a molecule of PEG?
..................................................................................................................................
(ii) Suggest why a liposome can carry more drug molecules than a molecule of PEG.
..................................................................................................................................
..................................................................................................................................
[2]
(e) Better-targeted delivery of drugs allows smaller amounts to be used, which brings
significant advantages.
Suggest two advantages of using smaller drug doses.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
[Total: 10]
(a) ester or amide (allow nitrile)

(c) (i) hydrophilic drug at C (1)

hydrophobic drug at B both needed (1)
(ii) (at A) the drug would be exposed to attack / breakdown / digestion (1) [3]
(d) (i) at one of the –OH groups (1)
(ii) volume of sphere can be large or one PEG molecule can only carry 1 or 2 drug
molecules (1)
or can carry different types of drug [2]
(e) more economic (1)
less chance of side-effects / side effects reduced / less chance of allergic reaction (1)
less risk of harming healthy tissue / organs / less chance of an overdose (1)
(3 max 2) [2]
[Total: 10]
Q. The design and development of batteries has been a major research area in recent
years.
(a) Lead-acid batteries, used in cars, are made up of a number of rechargeable cells in
series, and were first developed in 1860. They have the disadvantage of a relatively high
mass compared to the energy stored. During discharge, the electrode reactions in the
cells of these batteries are as follows.

State which of these reactions occurs at the positive electrode in a lead-acid cell during
discharge, explaining your answer.
..........................................................................................................................................
...................................................................................................................................... [1]
(b) Use the Data Booklet and the equations I and II above to calculate the voltage produced
by a lead-acid cell under standard conditions.
[2]
(c) Nickel-metal hydride batteries were developed in the 1980s and have become
increasingly common particularly for small devices such as mobile phones and digital
cameras that need near-constant sources of electrical energy. These cells use nickel
oxohydroxide (NiO(OH)) as one electrode and a hydrogen-absorbing alloy such as LiNi5
as the other electrode.
One reaction that takes place in these batteries is

(i) State the oxidation state of nickel in NiO(OH). .....................

(ii) Suggest a likely advantage of these batteries compared with lead-acid batteries.
..................................................................................................................................
..................................................................................................................................
[2]

(d) Hydrogen fuel cells have been suggested as the next major advance in electrically
powered vehicles. In these fuel cells hydrogen is oxidized to produce water, using a
catalyst and inert electrodes.
(i) Suggest a material for the electrodes.
..........................................................................
(ii) Use your knowledge of hydrogen to suggest a disadvantage of these fuel cells in
powering vehicles.
..................................................................................................................................
..................................................................................................................................
[2]
(e) Many of the world’s countries are developing ways of recycling materials which are
valuable or which require large amounts of energy to produce.
For each of the following recyclable materials, state whether recycling of this material is
important in saving energy or in saving resources. Use your knowledge of chemistry to
explain each choice.
glass ................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
steel .................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
plastics .............................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
[3]
[Total: 10]

Q. (a) NMR spectroscopy and X-ray crystallography are two techniques that use
electromagnetic radiation to look at the structures of large molecules. 9701/41/O/N/10/Q8

For each technique state the sub-atomic particle involved, and explain how this particle
interacts with the radiation.
NMR..................................................................................................................................
..........................................................................................................................................
X-ray .................................................................................................................................
..........................................................................................................................................
[4]
(b) The two NMR spectra 1 and 2 were obtained before and after an alcohol, Y, was oxidised
to give compound Z. The numbers of hydrogen atoms responsible for each peak have
not been shown. All the peaks have been shown.
(i) State which spectrum, 1 or 2, was produced by the alcohol, giving a reason for your
answer.
spectrum ....................................
reason .......................................................................................................................
..................................................................................................................................
(ii) The mass spectrum of Y showed an M : M + 1 peak ratio of 17.6:0.6.
Use this and other information in the question to suggest the identities of both Y
and Z.
(iii) Draw a displayed formula for Y in the box provided

(iv) Explain why the NMR spectrum of Z only shows one peak.
..................................................................................................................................
..................................................................................................................................
[7]
[Total: 11]

(a) Protons (1)

in NMR, energy is absorbed due to the two spin states (1)
Electrons (1)
in X-ray crystallography, X-rays are diffracted (by regions of high electron density) (1) [4]
(b) (i) 1 – no mark
The spectrum of alcohol / Y contains different peaks
Alcohol / Y contains different chemical environments
Spectrum 2 contains only one peak (1)
(ii) Spectrum 2 only shows 1 peak so Z must be a ketone (1)
Hence Y must be a 2° alcohol (1)
Q. A possible source of energy for the road vehicles of the future is hydrogen. One of the
problems still to be solved is the storage of the hydrogen in the vehicle. A conventional tank
holding liquid hydrogen would have to be pressurised and refrigerated. In a crash, this type
of tank could break resulting in the rapid release of hydrogen and an explosion. 9701/41/O/N/10/Q9

One alternative is to use a fuel tank packed with carbon nanotubes. The hydrogen in the tank
would be adsorbed onto the surface of the nanotubes at a pressure of no more than a few
atmospheres.
(a) (i) What is the approximate width of a carbon nanotube?
..................................................................................................................................
(ii) In what structural form is the carbon in a nanotube?
..................................................................................................................................
(iii) What forces could be responsible for holding the hydrogen on the surface of the
nanotubes? Explain your answer.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
(b) The hydrogen atoms in a fuel tank packed with nanotubes are closer together than in
liquid hydrogen. Suggest one advantage of this.
..........................................................................................................................................
...................................................................................................................................... [1]
(c) When a nanotube-packed fuel tank is full of hydrogen there is a steady pressure of
hydrogen in the tank. While hydrogen gas is being removed from the fuel tank to power
the car, the pressure in the fuel tank drops very little for some time. State Le Chatelier’s
principle, and suggest how it explains this observation.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [4]
[Total: 9]

(a) (i) A few nanometres (accept 0.5–10 nm) (1)

(ii) Graphite/graphene (1)
(iii) van der Waals’ (1)
Carbon atoms in the nanotubes are joined by covalent bonds (1)
(as are the hydrogen atoms in a hydrogen molecule)
or no dipoles on C or H2 or the substances are non-polar [4]
(b) More hydrogen can be packed into the same space/volume (1) [1]
(c) If a system at equilibrium is disturbed, the equilibrium moves in the direction which tends to
reduce the disturbance (owtte) (1)
When H2 is removed the pressure drops and more H2 is released from that adsorbed (1)

Equilibrium shifts to the right as pressure drops (1) [4]

[Total: 9]

Q. Instrumental methods of analysis have become increasingly important in recent years.

The use of chromatography to separate substances, and NMR spectroscopy to identify them,
has become routine in many laboratories. 9701/43/O/N/10/Q10

(a) Chromatography relies on either partition or adsorption to help separate substances.

(i) Briefly explain how each method brings about separation.
partition ....................................................................................................................
..................................................................................................................................
adsorption ................................................................................................................
..................................................................................................................................
(ii) The table shows three different techniques of chromatography. Identify which
separation method, partition or adsorption, applies to each.

(iii) The diagram represents the output from gas/liquid chromatography carried out on
a mixture.

Determine the percentage of each of the two components X and Y in the mixture.
[5]

(b) NMR spectroscopy is a very important analytical technique for use with organic
compounds.
(i) Why is NMR spectroscopy particularly useful for organic compounds?
..................................................................................................................................
..................................................................................................................................
(ii) Two molecules, propanal and propanone, have the same molecular formula,
C3H6O. Draw the displayed formula of each compound and explain briefly how
NMR spectroscopy can distinguish between the two structures.
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
..................................................................................................................................
[4]
[Total: 9]

(a) (i) Partition – substance is distributed between the stationary and mobile phase
or has different solubility in each phase (1)
Adsorption – substances form bonds of varying strength with or are attracted to
or are held on to stationary phase. (1)
(b) (i) They are largely composed of (carbon and) hydrogen which are active in the NMR
(owtte) or protons/H+/H exist in different chemical environments (with characteristic
absorptions) (1)
(ii) 2 correct displayed formulae (1)
In propanone all the protons are in a similar chemical environment (and hence there will
be one proton peak.) (1)
In propanal there are (three) different chemical environments and hence there will be
(three) proton peaks or three different chemical environments or three proton peaks (1)
[4]
[Total: 9]

Q. One of the greatest challenges facing scientists today is the development of effective
drugs to treat different forms of cancer.
(a) Drugs can be introduced into the body by injection or by mouth. Taking drugs by injection
avoids the drug being broken down in the digestive system.
State two other advantages of giving drugs by injection.
..........................................................................................................................................
..........................................................................................................................................
..........................................................................................................................................
...................................................................................................................................... [2]
(b) The drug Ultiva has been developed to treat ovarian cancer, and is usually given by
injection.
Study the structure of Ultiva and draw a circle around two different functional groups
that could be broken down in the digestive system. [2]
(c) One way of avoiding the breakdown of drugs in the body is to use a specially designed
nanoparticle which encloses the drug. If the nanoparticles are made of a particular sort
of polymer, they absorb water at the slightly acidic pH inside some cells, increasing their
diameter from around 100 nm to around 1000 nm. This spreads out the polymer chains
allowing release of the drug.
(i) Other than absorbing water, suggest a property this polymer would need to possess
for its use in drug delivery.
..................................................................................................................................
..................................................................................................................................
(ii) Why would this method of release not work if the nanoparticles were taken by
mouth?
..................................................................................................................................
[2]

(d) Polymers may be formed by two different types of chemical reaction.

Name the two types of reaction and write an equation to illustrate each reaction type.
name ....................................................
equation ...........................................................................................................................
name ....................................................
equation ...........................................................................................................................
[3]
(e) The breakdown of polymers, such as carbohydrates and proteins in the body is important
for digestion. What type of reaction is generally involved?
...................................................................................................................................... [1]
[Total: 10]

(a) Any two from:

The drug can be localised in a part of the body (1)
Smaller doses can be given reducing cost (1)
Smaller doses can be given with fewer possible side effects (1)
More immediate action / acts faster (1) [2]
 (c) (i) Must not react with the drug or must not breakdown too easily/quickly (1)
(ii) The swelling/hydrolysis would begin in the stomach (and the drug would be released too
soon) or stomach is acidic or has low pH (1) [2]
(d) Addition, condensation (1)
Suitable equation for addition (1)
Suitable equation for condensation (1)
(Addition equation must show polymeristion and balance – allow nX → X2n or Xn or Xn/2)
(Condensation can be simple reaction e.g. to single ester or amide but must balance –
2 products)
(If polymerisation RHS must show a repeat unit but can leave out other product – HCl etc.)
[3]
(e) Hydrolysis (1) [1]
[Total: 11]