Chemistry

Higher level
Paper 3

2 November 2023

Zone A morning Zone B morning Zone C morning

Candidate session number

1 hour 15 minutes

Instructions to candidates
Write your session number in the boxes above.
Do not open this examination paper until instructed to do so.
Answers must be written within the answer boxes provided.
A calculator is required for this paper.
A clean copy of the chemistry data booklet is required for this paper.
The maximum mark for this examination paper is [45 marks].

Section A Questions
Answer all questions. 1

Section B Questions
Answer all of the questions from one of the options.
Option A — Materials 2–5
Option B — Biochemistry 6 – 11
Option C — Energy 12 – 15
Option D — Medicinal chemistry 16 – 19

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37 pages © International Baccalaureate Organization 2023

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Section A

Answer all questions. Answers must be written within the answer boxes provided.

1. Pasteurization is used to eliminate pathogenic bacteria. The concentration of vitamin C was

monitored over a period of time in pasteurized and unpasteurized orange juice.

500
Unpasteurized orange juice
Pasteurized orange juice
450
Concentration of vitamin C/ g cm–3

400

350

300

250

200

150

100
0 7 14 21 28 35 42 49 56
Storage time / days

√
(a) (i) Identify the dependent variable represented in the graph. [1]

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(ii) Calculate the decrease in the concentration of vitamin C, in g cm 3, caused by

pasteurization. [1]

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(Question 1 continued)

(iii) Calculate the average rate of decrease of vitamin C concentration for pasteurized
juice, in g cm 3 day 1, for the first 56 days. [1]

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(iv) Deduce, referring to the graph, whether pasteurization affects the rate of change
of vitamin C concentration during storage of orange juice. [1]

√
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(v) The absolute uncertainty in each vitamin C concentration measurement was

2 g cm 3. Deduce, with a reason, whether the concentration of vitamin C in
pasteurized or unpasteurized orange juice has a larger percentage uncertainty. [1]

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(Question 1 continued)

(b) UV treatment is an alternative to pasteurization that minimizes loss of nutritional components.

(i) Deduce the type of electromagnetic radiation absorbed in the absorption

spectrum of vitamin C. Use section 3 of the data booklet.

1.2

1.0

0.8
Absorbance

0.6

0.4

0.2

0.0
250 300 350 400 450 500 550 600 650 700
220
Wavelength / nm [1]

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(ii) Deduce, giving a reason, the colour of vitamin C. [1]

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(iii) Suggest why the use of UV light is not effective for the elimination of pathogenic
bacteria in orange juice. [1]

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(Question 1 continued)

(iv) Identify two ways to decrease the rate of change of vitamin C concentration due
to oxidation during the storage of orange juice. [2]

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(c) The concentration of vitamin C and pH of different fruits were measured.

Concentration of
pH
vitamin C / mg dm 3
Watermelon 29 5.07

Banana 46 5.05

Apple 69 4.18

Pineapple 139 3.51

Orange 185 4.25

Deduce, with a reason, whether the data show a correlation between concentration of
vitamin C and pH. [1]

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t
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(Question 1 continued)

(d) The concentration of vitamin C (ascorbic acid) can be measured by performing a redox
titration using acidified iodate, IO3 , and iodide ions. Starch reacts with excess iodine
once the vitamin C is consumed to produce a dark-blue complex.

Reaction 1: IO3 (aq) 5I (aq) 6H (aq) 3I2 (aq) 3H2O (l)

Reaction 2: ascorbic acid (aq) I2 (aq) 2I (aq) dehydroascorbic acid (aq)

(i) Identify the oxidizing agent in reaction 1. [1]

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

(ii) The student recorded the end point and then noticed the blue colour in the
conical flask disappeared. Suggest why this occurred. [1]

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

× Y
..........................................................................

(iii) State the effect the recorded end point has on the value of the calculated
concentration of vitamin C. [1]

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

(iv) Suggest why this method cannot be used to measure the concentration of
vitamin C in blueberry juice. [1]

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Section B

Answer all of the questions from one of the options. Answers must be written within the answer boxes
provided.

Option A — Materials

2. Sodium hydride forms a crystalline lattice.

(a) Deduce, giving a reason, whether sodium hydride could be classified as a Brønsted–Lowry
acid or a Brønsted–Lowry base. [1]

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(b) Materials with high ion-exchange capacity, such as zeolites, can be used to soften
water by replacing calcium ions with sodium ions. Outline two reasons for using
zeolites for ion exchange. [2]

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(Option A continued)

3. Properties of materials are dependent upon their chemical structure.

(a) Outline why polar molecules can exhibit liquid crystal behaviour. [2]

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(b) Suggest why double walled carbon nanotubes are excellent conductors of heat along
the tube but poor conductors across the width of the tube. [2]

[Source: iStock.com/ollaweila.]

Good conductors along the length of the tube:

..........................................................................
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Poor conductors across the width of the tube:

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(Option A, question 3 continued)

(c) Outline how an inductively coupled plasma (ICP) torch converts argon into plasma. [3]

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(d) (i) Contrast the physical properties of polymers with extensive covalently bonded
cross-links to polymers which only have a few of these links, giving an example
of each. [4]

Physical properties Example

Extensive
covalent ............................... ...............................
cross-links:
............................... ...............................
............................... ...............................
............................... ...............................

Few covalent
cross-links: ............................... ...............................
............................... ...............................
............................... ...............................
............................... ...............................

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(Option A, question 3 continued)

(ii) Kevlar® has extensive hydrogen bond cross-links. The polymer can be formed
from benzene 1,4-dicarboxylic acid and benzene-1,4-diamine.

H O C C O H H N N H

O O H H

Draw one repeating unit of Kevlar®. [1]

(iii) Suggest two reasons for the degradation of Kevlar® on contact with
concentrated acids. [2]

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(iv) Suggest one Resin Identification Code (RIC) for a non-recyclable plastic, with a
reason for it not being recycled. Use section 30 of the data booklet. [1]

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(Option A continued)

4. Copper can be obtained by electrolysis as well as precipitation.

(a) An experiment to calculate Faraday’s constant (F) was performed by electrolysing a

solution of copper(II) sulfate using pure copper electrodes. A charge of 900.0 C was
passed through the cell resulting in a mass loss of 0.296 g at the anode.

Power supply

A Ammeter

Beaker

Anode Cathode
(copper) (copper)

Copper(II) sulfate
solution

Suggest why mass gained at the cathode is a less accurate measure of electrolysed
copper than mass loss at the anode. [1]

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

(b) Calculate a value for Faraday’s constant from this experiment. [2]

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(Option A, question 4 continued)

(c) Copper can be removed from solution by precipitating aqueous Cu2 ions as
copper(II) hydroxide.

Calculate the molar solubility of Cu2 (aq) in a solution of pH 10.00.

20
Ksp Cu(OH)2 2.2 10 [2]

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(d) D-penicillamine is a chelating agent used to remove excess copper in people suffering
from Wilson’s disease. Explain how D-penicillamine chelates as a bidentate ligand
with Cu2 .

CH3 H
O
H 3C C C C
OH
SH NH2
D-penicillamine [3]

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(Option A continued)

5. Superconducting Magnetic Levitation (MAGLEV) trains use a niobium–titanium alloy that

becomes a Type 2 superconductor when cooled with liquid helium.

(a) Outline one difference between Type 1 and Type 2 superconductors. [1]

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(b) Explain how superconductivity occurs in terms of Bardeen–Cooper–Schrieffer

(BCS) theory. [3]

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End of Option A

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Option B — Biochemistry

6. A variety of methods are used to analyse proteins.

(a) State the type of bonding involved in the primary level of protein structure. [1]

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

(b) (i) Outline how to use paper chromatography to identify the composition of amino
acids in a polypeptide. [3]

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(ii) Isoleucine was identified as one of the amino acids. Draw the structure of the
predominant form of this amino acid at pH 4.50. Use section 33 of the
data booklet. [1]

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(Option B, question 6 continued)

(c) The calibration curve for the absorbance of dyed protein, at 595 nm, as a function of
concentration is given.

0.8000
y 0.3826x 0.0015
0.7000

0.6000

0.5000
Absorbance

0.4000

0.3000

0.2000

0.1000

0.0000
0.00 0.50 1.00 1.50 2.00
Protein concentration / mg cm–3

Calculate, using the linear equation, the concentration of protein in a sample with an
absorbance of 0.5000. [1]

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(Option B continued)

7. Phosphatidylserine is an example of a phospholipid.

(a) Phosphatidylserine may be formed from propane-1,2,3-triol, 2 oleic acid molecules,

phosphoric acid and the serine anion.

H 2C OH NH2

HC OH 2C17H33COOH H3PO4 HOCH2CHCOO 4H2O phosphatidylserine

H 2C OH

Sketch the structural formula of phosphatidylserine. [2]

H 2C

HC

H 2C

(b) (i) Phosphatidylserine can be composed of different fatty acids such as stearic acid
and linoleic acid.

Predict, giving two reasons, which of these fatty acids would have a higher
melting point. Use section 34 of the data booklet. [2]

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(Option B, question 7 continued)

(ii) Suggest one advantage and one disadvantage of the hydrogenation of vegetable
oil by the food industry. [2]

Advantage:
..........................................................................
..........................................................................

Disadvantage:
..........................................................................
..........................................................................

(c) Contrast the processes of hydrolytic and oxidative rancidity in fats with respect to the
site of reactivity and conditions, other than temperature, that favour reaction. [2]

Hydrolytic rancidity Oxidative rancidity

Site of
reactivity: ............................... ...............................
............................... ...............................

Conditions
that favour ............................... ...............................
reaction:
............................... ...............................

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(Option B continued)

8. Lactose is the main disaccharide in milk.

(a) Lactose is composed of galactose and glucose.

CH2OH CH2OH

OH O OH H O H
H H
OH H OH H
H OH
H OH

H OH H OH
Galactose Glucose

(i) Draw the structure of lactose. [2]

O O

(ii) State the type of reaction that forms the disaccharide from monosaccharides. [1]

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(Option B, question 8 continued)

(b) (i) Lactase is the enzyme that converts lactose into the monosaccharides.

Sketch a curve to show how the activity of lactase varies when a competitive
inhibitor is present. [1]

No inhibitor
present
Rate of reaction

Lactose concentration

(ii) State, giving a reason, the effect of the competitive inhibitor on the value of Km. [1]

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(c) Milk is fortified with vitamin D. State a disease related to vitamin D deficiency. [1]

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(Option B continues on page 23)

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(Option B continued)

9. Host–guest chemistry has been used for the removal of xenobiotics in the environment.

(a) Outline what is meant by xenobiotic. [1]

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(b) Compare the bonding of synthetic host molecules and enzymes to substrates. [1]

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(c) Suggest a specific environmental application of host–guest chemistry. [1]

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(Option B continued)

10. Anthocyanins, such as oenin, are pigments in plants.

OCH3

OH

HO O
OCH3

OH
O O

OH HO OH
HO

oenin

(a) The absorption spectrum of oenin, taken in acidic condition, is given.

Absorbance

200 300 400 500 600 700

Wavelength / nm

Identify, giving a reason, the colour of a plant containing oenin. Use section 17 of the
data booklet. [2]

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(Option B, question 10 continued)

(b) Explain how oenin acts as an acid–base indicator. Refer to its structure. [2]

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11. Cells contain both DNA and RNA.

(a) Contrast two differences between the structures of DNA and RNA. [2]

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(b) It is now possible to send a sample of DNA for analysis and receive results of ancestral
background. Every year these results are more accurate. Suggest how this is possible
even though the technology has not changed. [1]

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End of Option B

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Option C — Energy

12. The spontaneity of nuclear fission and fusion reactions can be explained by changes in
nuclear binding energy.

(a) State what is meant by nuclear binding energy. [1]

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(b) (i) A deuteron, or deuterium nucleus, 2H, has a mass of 3.343583 10 27 kg.
Determine the nuclear binding energy of deuteron, in J, using E mc2 and
section 4 of the data booklet. [2]

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(ii) Determine the energy released, in MeV, when a helium-4 nucleus (4He) is formed
from deuteron (2H) and triton (3H). Use section 36 of the data booklet.
2 3 4 1
1 H 1 H 2 He 0 n [2]

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(c) (i) The average energy release in the fission of one atom of 235U is 193.4 MeV.
Calculate the specific energy of 235U in MJ per gram.

19
1 MeV 1.60 10 MJ. [1]

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. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .←
..............................
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(Option C, question 12 continued)

(ii) Explain whether the energy density, in MJ dm 3, or specific energy, in MJ kg 1, of

hydrogen has a higher value at standard conditions of temperature and pressure. [1]

←
..........................................................................
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(d) (i) Write the nuclear alpha decay equation of 235U forming a helium-4 nucleus and a
product with a much shorter half-life. [1]

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(ii) The half-life of the product is 25.5 hours. Calculate the time taken, in hours, for

√
1.000 g of the product to decay to 0.03125 g. [2]

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(Option C continued)

13. Many molecules interact with light.

(a) (i) Contrast, at the molecular level, how carbon dioxide and a coloured pigment,
such as chlorophyll, interact with electromagnetic radiation. [4]

V
Carbon dioxide:
..........................................................................
..........................................................................
..........................................................................

Chlorophyll:
..........................................................................
..........................................................................
-

z
..........................................................................

(ii) Identify the range of wavelengths absorbed by carbon dioxide and chlorophyll.
Use section 3 of the data booklet. [1]

Carbon dioxide:
..........................................................................

Chlorophyll:
..........................................................................

(b) Upper atmosphere temperatures recorded by satellites are becoming lower over time.

Suggest how greenhouse gases could be responsible for this trend. [2]

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(Option C, question 13 continued)

(c) Explain the high efficiency of dye-sensitized solar cells (DSSC) which use
nanoparticles coated with a black dye. [2]

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w
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(Option C continued)

14. Natural gas is a fossil fuel.

(a) State the chemical process by which fossil fuels were formed from biological compounds. [1]

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(b) State the main component of natural gas. [1]

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(c) Outline one advantage and one disadvantage, apart from cost, of using natural gas
over other fossil fuels. [2]

Advantage:
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Disadvantage:
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(d) Suggest a reason why syngas, produced from coal or biomass gasification, may be
considered a viable alternative to crude oil. [1]

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(Option C continued)

15. Electrochemical cells generate electricity from a spontaneous redox reaction.

(a) Species of Geobacter bacteria can be used in microbial fuel cells to oxidize aqueous
ethanoate ions, CH3COO (aq), to carbon dioxide gas. Deduce the half-equations for
the reactions, in acidic conditions, at both electrodes. [2]

Negative electrode (anode):

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Positive electrode (cathode):

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(b) Describe, in detail, how both fuel cells and secondary cells can be reused. [2]

Fuel cells:
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√
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Secondary cells:
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(c) Calculate the cell potential (E), in V, of a voltaic cell which consists of a magnesium
electrode in a solution of 2.00 mol dm 3 Mg2 (aq) and a silver electrode in a solution of
0.0100 mol dm 3 Ag (aq). Use sections 1 and 24 of the data booklet. [2]

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End of Option C
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Option D — Medicinal chemistry

16. Aspirin and morphine are two analgesics.

(a) State the site and mode of action of aspirin. [2]

Site of action:
..........................................................................

Mode of action:
..........................................................................
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(b) (i) Aspirin is synthesized from salicylic acid. Discuss two ways in which the melting
point of crystallized aspirin can indicate the presence of impurities. [2]

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(ii) Deduce the range of wavenumbers in the IR spectrum which would indicate
that the impure aspirin contains salicylic acid. Use sections 26 and 37 of the
data booklet.
O

OH

OH
Salicylic acid [1]

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(Option D, question 16 continued)

(c) Morphine can be administered both orally and intravenously.

Suggest one reason why drugs administered orally have lower bioavailability than
drugs administered intravenously. [1]

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

(d) Morphine has a much greater affinity for the opioid receptor in the central nervous
system compared to diamorphine.

Explain why diamorphine is a more potent analgesic. Use section 37 of the data booklet. [2]

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(e) Deduce, giving two reasons, whether the product is morphine or diamorphine,
referring to structure and the spectrum. Use sections 26 and 37 of the data booklet.

1.0

0.8
Transmittance

0.6

0.4

0.2

0.0
4000 3000 2000 1000
Wavenumber / cm–1 [2]

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(Option D continued)

17. Excess stomach acid is a common health condition.

(a) Explain how omeprazole regulates stomach pH. [2]

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(b) Write an equation for the reaction of a solution of sodium hydrogen carbonate with
stomach acid, including state symbols. [1]

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(c) Predict, with a reason, whether the neutralization of acid by ranitidine in a titration is a
reliable measure of its effectiveness in regulating stomach acid. [1]

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(d) Deduce, giving a reason, whether the 1H NMR spectrum of oseltamivir or omeprazole
has signals with chemical shifts in the 7.0 8.1 ppm range. Use sections 27 and 37 of
the data booklet. [1]

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(Option D continues on the following page)

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(Option D continued)

18. Viruses and bacteria must be targeted in different ways.

(a) (i) Describe how oseltamivir (Tamiflu) works as a preventative agent against
flu viruses. [2]

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(ii) The production of oseltamivir requires shikimic acid, a precursor originally

obtained from star anise.
Comment on an advancement made in the production of shikimic acid and its
importance in terms of green chemistry. [2]

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(b) (i) Describe the role of the beta-lactam ring in the action of penicillin against bacteria. [2]

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(ii) State a consequence of bacteria gaining increased resistance to antibiotics. [1]

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(Option D continued)

19. Radiotherapy and chemotherapy are two approaches to cancer treatment.

(a) (i) State a common side effect of radiotherapy. [1]

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(ii) State one advantage of using a gamma emitter over a beta emitter in nuclear
medicine. [1]

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

(iii) Write an equation for the beta decay of Lutetium-177. [1]

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(iv) A typical dose of Lu-177 is 2.00 g and its half-life is 6.71 days. Determine the
mass of Lu-177, in g, remaining after one week. Use section 1 of the data booklet. [2]

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(Option D continues on the following page)

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(Option D, question 19 continued)

(b) (i) Taxol, a drug used in chemotherapy, is synthesized using chiral auxiliaries.
Describe how the chiral auxiliary is used to produce the desired product. [2]

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

(ii) Mass spectroscopy of taxol (Mr 854) shows an m/z peak at 836. Suggest a
fragment, the loss of which could be responsible for this peak. Use section 28 of
the data booklet.

O
CH3
O O
CH3 OH

H 3C CH3
O NH O
CH3

O O
OH O O
OH CH3

O
O

Taxol [1]

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End of Option D

40EP37
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Content used in IB assessments is taken from authentic, third-party sources. The views expressed within them belong to their
individual authors and/or publishers and do not necessarily reflect the views of the IB.

References:

1. Oulé, M., Dickman, M., Arul, J., 2013. Properties of Orange Juice with Supercritical Carbon Dioxide Treatment.
[graph] Available at: https://www.researchgate.net/publication/263368607_Properties_of_Orange_Juice_with_
Supercritical_Carbon_Dioxide_Treatment [Accessed 4 May 2020]. Source adapted.

1(b)(i). Koutchma, T., 2010. UV irradiation improves safety of foods and beverages. [graph] Available at: https://www.
researchgate.net/figure/Measured-absorption-spectra-of-apple-juice-and-vitamin-C-as-well-as-emission-spectra-
of_fig1_274630712 [Accessed 4 May 2020]. Source adapted.

1(c). Unaegbu, M., Godwill, E. A., et al., 2016. Heavy metal, nutrient and antioxidant status of selected fruit samples
sold in Enugu, Nigeria. [table] Available at: https://www.researchgate.net/figure/pH-acidity-ascorbic-acid-and-
antioxidantactivity-of-fruit-samples_tbl2_305691722 [Accessed 4 May 2020]. Under creative commons CC BY 4.0
DEED licence. https://creativecommons.org/licenses/by/4.0/. Source adapted (table simplified and redrawn).

3(b). iStock.com/ollaweila.

6(c). Chowdry, T. Variability and inheritance of proteins in Apris mellifera eggs. “BSA Calibration Curve” [graph] Available
at: https://www.researchgate.net/publication/235329683_Variability_and_inheritance_of_proteins_in_Apis_mellifera_
eggs [Accessed 4 May 2020]. Source adapted.

10(a). NotWith, 2012. Spectra Chlorophyll ab oenin. [graph] Available at: https://en.wikipedia.org/wiki/Anthocyanin#/media/
File:Spectra_Chlorophyll_ab_oenin_(1).PNG [Accessed 4 May 2020]. Licensed under the Creative Commons
Attribution-Share Alike 3.0 Unported license https://creativecommons.org/licenses/by-sa/3.0/deed.en. Source adapted
(redrawn and simplified).

16(e). Reprinted with permission from NIST © United States of America as represented by the Secretary of Commerce.
Graph redrawn.

All other texts, graphics and illustrations © International Baccalaureate Organization 2023

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