M19/4/CHEMI/HP3/ENG/TZ2/XX

Chemistry
Higher level
Paper 3

Thursday 23 May 2019 (morning)

Candidate session number

1 hours 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. 1–2

Section B Questions
Answer all of the questions from one of the options.
Option A — Materials 3–8
Option B — Biochemistry 9 – 13
Option C — Energy 14 – 20
Option D — Medicinal chemistry 21 – 27

2219 – 6115
33 pages © International Baccalaureate Organization 2019

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Option D — Medicinal chemistry

21. Medicines and drugs are tested for effectiveness and safety.

(a) Distinguish between therapeutic window and therapeutic index in humans. [2]

(b) Explainwindow:
Therapeutic why diamorphine (heroin) is more potent than morphine using section 37 of the
data booklet. [2]
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Therapeutic index:
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(Option D continued)

22. A student synthesized aspirin, acetylsalicylic acid, in a school laboratory.

C
OH

C
H3C O

Aspirin
Mr  180.17

(a) Predict one absorption band present in an infrared (IR) spectrum of aspirin, using
section 26 of the data booklet. [1]

(b)
. . . . 0.300
. . . . . g. .of
. .crude
. . . . .aspirin
. . . . . .was
. . . dissolved
. . . . . . . . in
. . ethanol
. . . . . . .and
. . .titrated
. . . . . . with
. . . . sodium
. . . . . . .hydroxide
..........
solution, NaOH (aq).
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NaOH (aq)  C9H8O4 (in ethanol)  NaC9H7O4 (aq)  H2O (l)

(i) Determine the mass of aspirin which reacted with 16.25 cm3 of 0.100 mol dm3
NaOH solution. [2]

. . . . (ii)
. . . . . .Determine
. . . . . . . . .the
. . percentage
. . . . . . . . . .purity
. . . . .of
. . the
. . . synthesized
. . . . . . . . . .aspirin.
....................... [1]

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

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(Option D continues on the following page)

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(Option D, question 22 continued)

(c) Outline how aspirin can be chemically modified to increase its solubility in water. [1]

(d)
. . . . State
. . . . .why
. . . .aspirin
. . . . . .should
. . . . . .not
. . .be
. . taken
. . . . .with
. . . .alcohol.
................................... [1]

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23. Excess acid in the stomach can cause breakdown of the stomach lining.
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(a) (i) Outline how ranitidine (Zantac) inhibits stomach acid production. [1]

. . . . (ii)
. . . . . .Outline
. . . . . . two
. . . . advantages
. . . . . . . . . of
. . .taking
. . . . . ranitidine
. . . . . . . . instead
. . . . . . .of. .an
. . antacid
. . . . . . which
............
neutralizes excess acid. [2]
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(Option. .D. .continues

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. . .the
. . . following
. . . . . . . . . .page)
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(Option D, question 23 continued)

(b) Some antacids contain carbonates.

Determine the pH of a buffer solution which contains 0.160 mol dm3 CO 2
and
3
3 
0.200 mol dm HCO , using section 1 of the data booklet.
3

pK (HCO )  10.32 [1]

a

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24. Antiviral medications have recently been developed for some viral infections.
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(a). . . . Outline
. . . . . . .one
. . . . way
. . . .in. .which
. . . . . antiviral
. . . . . . . .drugs
. . . . work.
.................................... [1]

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(b)
. . . . Discuss
. . . . . . . two
. . . . difficulties
. . . . . . . . . associated
. . . . . . . . .with
. . . . solving
. . . . . . the
. . . AIDS
. . . . . .problem.
...................... [2]

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(Option. .D. .continues

. . . . . . . . . .on
. . .the
. . . following
. . . . . . . . . .page)
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(Option D
25. Taxol is a drug that was once obtained from yew trees and is now produced using chiral auxiliaries.

(a) Examine the synthesis of taxol in terms of green chemistry criteria. [2]

(b)
. . . . Outline
. . . . . . .the
. . .operation
. . . . . . . .of
. . a. polarimeter
. . . . . . . . . . used
. . . . to
. . distinguish
. . . . . . . . . .between
. . . . . . .enantiomers.
................ [2]

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(Option.. ..D.. ..continues

.. .. .. .. .. .. .. .. .. ..on
.. .. ..the
.. .. .. following
.. .. .. .. .. .. .. .. .. ..page)
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(Option D
26. Technetium-99m, Tc-99m, is a gamma-ray emitter commonly used as a medical tracer. Its
half-life is 6.0 hours.

(a) Evaluate the suitability of technetium-99m for this use. [2]

(b)
. . . . Calculate
. . . . . . . . the
. . . percentage
. . . . . . . . . of
. . .technetium-99m
. . . . . . . . . . . . . remaining
. . . . . . . . .after
. . . .10.0
. . . .hours.
. . . . . Use
. . . .section
. . . . . . 1. .
of the data booklet. [2]
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(Option. .D. .continues
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. . .the
. . . following
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(Option D
27. The presence of alcohol in the breath can be detected using a breathalyser.

(a) Describe how a fuel cell breathalyser works. [3]

(b)
. . . . Alcohol
. . . . . . . levels
. . . . . .in. .the
. . .breath
. . . . .can
. . . also
. . . . be
. . determined
. . . . . . . . . .using
. . . . .IR
. . spectroscopy.
.....................
. . . . Suggest,
. . . . . . . .giving
. . . . . a. .reason,
. . . . . .which
. . . . . bond’s
. . . . . . absorbance
. . . . . . . . . .is. .most
. . . . useful
. . . . . .for
. . detecting
. . . . . . . . ethanol
......
. . . . in
. . breath.
.................................................................... [2]

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Bond:
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. . . . . . . . . . . . . . . . . . . . . . . . . . . . . End
. . . . . . of
. . . .Option
. . . . . . . . . .D
.........................

Reason:
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