CHEM 100/100G

THE UNIVERSITY OF AUCKLAND

SUMMER SCHOOL 2019

Campus: City

CHEMISTRY

Molecules that Changed the World

(Time Allowed: TWO hours)

NOTE: Answer QUESTION ONE in SECTION A and ONLY THREE of the FOUR
questions in SECTION B.
Write all your answers in the booklet provided.

Page 1 of 11
 CHEM 100/100G

SECTION A: Answer QUESTION ONE

QUESTION ONE (answer ALL parts a-q):

(a) Match the names of these chemicals with their description. Write the compound that
matches the description for each question number in your script.

 norethindrone
 ascorbic acid
 piperine
 nitroglycerine

i) The main active compound in pepper that causes a hot sensation on the nervous
system.
ii) Another name for Vitamin C. If people (often sailors on long sea voyages) had a
deficiency in this, they would develop the disease called scurvy.
iii) When stabilised with diatomaceous earth is a useful explosive, dynamite,
developed by Alfred Nobel.
iv) A synthetic steroid that is an artificial progesterone and one of the first
contraceptive pills.
(0.5 marks each, 2 marks total)

(b) DDT and Thalidomide are both molecules that many would argue “changed the world”.
Choose one of these and briefly explain why it was so important to society and what
human health issues and environmental impacts your chosen molecule has.
(3 marks)

For parts (c)-(g) write the correct answer (A, B, C or D) in your script alongside the
question number.

(c) Which of these are drugs?

A: caffeine
B: cocaine
C: morphine
D: All of the above
(1 mark)

(d) Drugs have a specific molecular interaction with biomolecules within a host cell of an
invading organism. Which of these is NOT a biomolecule that drugs can target:
A: Carbohydrates
B: Nucleic acids
C: Blood
D: Proteins
(1 mark)

Page 2 of 11
 CHEM 100/100G

(e) Penicillin was first discovered by Alexander Fleming as a natural product produced by
what type of living organism?
A: Bacteria
B: Mould (a Fungi)
C: Marine sponge
D: Tree
(1 mark)

(f) During World War 2, the main contribution by the USA with regard to penicillin was:
A: Supply patients for clinical trials to test how effective it was.
B: Give money to UK researchers/scientists to produce penicillin.
C: Develop techniques to produce large quantities of penicillin.
D: Nothing – the USA did not contribute to the development of penicillin.
(1 mark)

(g) Which of the following statements about penicillin resistance is false?

A: Bacteria can become resistant to penicillin in a number of ways including
spontaneous genetic mutation, gene transfer of natural selection.
B: Penicillin resistant strains have only been seen in the past 5 years.
C: Penicillin resistance has increased because of widespread use and misuse.
D: There are other classes of antibiotics that can be used for the treatment of penicillin
resistance.
(1 mark)

(h) Explain the terms ‘polymer’ and ‘monomer’.

(2 marks)

(i) What type of chemical repeat unit is present in nylon?

(1 mark)

(j) Provide two similarities and two dissimilarities between nylon and low-density
polyethylene.
(2 marks)

(k) According to the International Union of Pure and Applied Chemistry (IUPAC), what is
the definition of alcohol?
(1 mark)

(l) According to the IUPAC definition, is the compound 1 an alcohol?

(1 mark)

(m) Draw the structure of methanol.

(1 mark)

Page 3 of 11
 CHEM 100/100G

(n) Is methanol a primary, secondary or tertiary alcohol?

(1 mark)

(o) Is t-butanol a primary, secondary or tertiary alcohol?

(1 mark)

(p) Explain why soap was a luxury item in the 17th Century, but by the 19th Century had
become a mass-produced product.
(2 marks)

(q) Define surfactant, and describe the features a molecule needs to have to be considered a
surfactant. Explain how a surfactant enables cleaning (a diagram may help).
(3 marks)

Total = 25 marks

Page 4 of 11
 CHEM 100/100G

SECTION B: Answer ANY THREE questions from QUESTIONS TWO-FIVE

QUESTION TWO: Penicillin (answer ALL parts a-e):

(a) Define the following terms:

i) Prodrug

ii) Lead compound

(2 marks each, 4 marks total)

(b) Before the discovery of penicillin, there were a number of scientists who greatly
contributed to the development of medicinal chemistry and our understanding of disease,
including:

 Edward Jenner
 Louis Pasteur
 Robert Koch
 Joseph Lister
 William Perkin
 Paul Ehrlich

Choose TWO of these scientists and briefly describe their contribution

(3 marks each, 6 marks total).

(c) The structures of general penicillin and D-Ala-D-Ala are given below:

i) Copy the structure of a general penicillin into your answer booklet and circle TWO
of the structural features essential for antibiotic activity.
(2 marks)

ii) Describe the mechanism of action of penicillin with reference to the structure of
D-Ala-D-Ala.
(6 marks)

Page 5 of 11
 CHEM 100/100G

(d) The structures of amoxycillin, 6-APA and clavulanic acid are shown below:

i) By referencing the structure of the natural product 6-APA, explain why

amoxycillin is considered to be “semi-synthetic”.
(2 marks)

ii) Amoxycillin is often co-administered with clavulanic acid as a way to

overcome penicillin resistance. Explain how this works.
(3 marks)

(e) State the names of two other classes of antibiotics besides the penicillins.
(2 marks)

Total = 25 marks

Page 6 of 11
 CHEM 100/100G

QUESTION THREE: Nylon (answer ALL parts a-e):

(a) For each point (i) – (x) listed in column A, write the most appropriate phrase from
Column B.

Column A Column B
i) Nylon 6  Semi-synthetic thermoplastic polymer
ii) Something silk and
 Synthetic thermoplastic copolymer
nylon have in common
iii) Nylon was invented by  Wallace Carothers
iv) Concept of
macromolecules was  Hermann Staudinger
first hypothesised by
v) Bakelite  Synthetic nonbiodegradable
homopolymer
vi) Rubber  Pleated sheet structure
vii) Acrylonitrile butadiene
 Amide linkage
styrene (ABS)
viii) Silk  Needs vulcanization process to form
the product
ix) Polylactic acid  Synthetic thermoset polymer formed
by condensation of phenol and
formaldehyde
x) Celluloid  Synthetic biodegradable polymer

(0.5 mark each, 5 marks total)

(b) True or False? Indicate your answers by writing “True” or “False” in the answer booklet
alongside the question number.

i) Nylon is denser than water.

ii) High density polyethylene has more chain branching than low density
polyethylene.
iii) A similar length and diameter of nylon fibre will be stronger than hemp fibre
but heavier in weight.
iv) The resin identification code of nylon 6 is ‘6’.
v) The Izod impact strength of nylon 6 is more than nylon 66.
vi) Hydrogen bonding forms between O-H and C=O groups in nylon.
vii) Nylon is an engineering polymer and can replace metal cogs due its lighter
weight and greater durability.
viii) Teflon is a hydrophilic polymer.
ix) A hemp plantation requires more water than a cotton plantation of the same size.
x) Cotton contains more than 90% cellulose.

(0.5 marks each, 5 marks total)

Page 7 of 11
 CHEM 100/100G

(c) Write the correct answer (A, B, C, or D) in the answer script alongside the question
number. Give only one best answer for each question:

i) Neil Armstrong planted a flag on the moon in 1969 which was made of
following plastic:
A: Polyester
B: Silk
C: Nylon
D: Polypropylene

ii) What plastics processing technology would be ideal to manufacture sturdy

large size hollow shaped products such as water storage tank?
A: Thermoforming
B: Blow moulding
C: Rotational moulding
D: Extrusion

iii) How many times can a Thermoset plastic be heated and shaped?
A: Once
B: Twice
C: Three times
D: Many times

iv) Nylon 6 can be synthesised by:

A: Condensation polymerisation
B: Photo polymerisation
C: Free radical polymerisation
D: Ring opening polymerisation

v) During the first 5 years of production, what was a major portion of nylon fibre
used for, especially during World War II?
A: Toothbrush bristles
B: Stockings
C: Parachutes
D: Carpeting
(1 mark each, 5 marks total)

(d) i) Between Nylon 6 and Nylon 66, which has a higher crystalline melting point?
(1 mark)

ii) How can we explain this based on molecular interaction?

(1 mark)

iii) Name three naturally occurring polymers or their sources that can be used to make
textile as an alternative to nylon.
(3 marks)

Page 8 of 11
 CHEM 100/100G

(e) i) What are the three general approaches to plastics waste disposal?
(3 marks)

ii) Which approach will be preferred for waste disposal of nylon commodities and
why?
(2 marks)

Total = 25 marks

Page 9 of 11
 CHEM 100/100G

QUESTION FOUR: Soap (answer ALL parts a-h):

(a) A hypothesis of how soap was discovered is that it was noticed clothes became
cleaner when washed downriver from where fat from animal sacrifices combined with ash
from fires. Describe the chemistry involved and comment on whether this is believable.
(3 marks)

(b) Vitruvius in the 1st Century BC considered that “poisonous breath of creatures of the
marshes” made a site next to a swamp unhealthy. Comment on the negative and positive
aspects of the fact that this view of disease was taken seriously for nearly 2000 years.
(4 marks)

(c) Explain why ice floats on liquid water.

(2 marks)

(d) Define surface tension. Explain why water has a high surface tension, and give an
example of how this might be observed.
(3 marks)

(e) Modern pesticides include surfactants in their formulations. Explain the role of the
surfactant.
(3 marks)

(f) Give a modern industrial use of a surfactant (other than in pesticides) and explain why
the surfactant is necessary.
(3 marks)

(g) Give a biological use of a surfactant, and explain why the surfactant is necessary.
(3 marks)

(h) Are we too obsessed with cleanliness? Explain why or why not.
(4 marks)

Total = 25 marks

Page 10 of 11
 CHEM 100/100G

QUESTION FIVE: Alcohol (answer ALL parts a-f):

(a) The consumption of methanol is toxic to humans.

i) The primary pathway to break down methanol inside our body involves two
enzymes. Name the two enzymes, and briefly describe the roles of these two
enzymes and the fate of the methanol.
(5 marks)

ii) Explain why methanol is toxic to humans.

(2 marks)

(b) Ethanol is used as a renewable energy source. Describe schematically the carbon
cycle involving ethanol as a biofuel.
(4 marks)

(c) Ethylene glycol is used as an antifreeze. Describe how ethylene glycol can lower the
freezing point of water.
(4 marks)

(d) Alcohol is used as a disinfectant.

i) Which is a more effective disinfectant: 100% alcohol or 70% alcohol / 30%

water mixture?
(1 mark)

ii) Explain the reasoning behind your answer.

(4 marks)

(e) Ethanol is the alcohol that is contained in alcoholic beverages. List three factors that
may affect the rate of absorption of ethanol in humans after consumption.
(3 marks)

(f) A breathalyzer is an instrument that is used by law enforcement officers to check the
blood alcohol concentration in breath during roadside tests. Potassium dichromate is an
essential component in a breathalyzer. Briefly describe its function.
(2 marks)

Total = 25 marks

Page 11 of 11