THE UNIVERSITY OF MELBOURNE

SCHOOL OF CHEMISTRY
Mock Exam 3
SUBJECT: CHEMISTRY FOR BIOMEDICINE, CHEM10006

Student Number: ___________________________

Exam Duration: 3 hours Reading Time: 15 minutes

This paper has 25 pages.

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CHEM10006 Mock Exam 3

SECTION A
A table of selected physical constants, useful quantities and conversion factors is provided at the end
of the exam paper in Appendix 1, structures of nucleobases in Appendix 2, structures of the 20
common amino acids in Appendix 3 and the D-aldohexose "family tree" in Appendix 4.

Question A1.

Initial rate data for a gaseous reaction at 298K is given below.

2A(g) + 2B(g) → C(g) + D(g)

[ A ]initial [ B ]initial Initial Rate

0.10 M 0.20 M 0.0150 M s–1
0.10 M 0.30 M 0.0225 M s–1
0.20 M 0.40 M 0.120 M s–1
What is the correct rate law for this reaction at 298 K?

A. rate = k [A]2 [B]

B. rate = k [A] [B]2

C. rate = k [A] [B]

D. rate = k [A]2 [B]2

E. rate = k [A]2 [B]1.5

(2 marks)

Question A2.

The reaction below is second-order with respect to A:

A→ B+ C

When [A]0 = 0.100 M, the reaction is 20.0% complete in 48.2 minutes. For this reaction, which
one of the following is the half-life closest to?
A. 2.41 × 104 min

B. 8.57 min

C. 1.93 × 102 min

D. 78.3 min

E. 16.1 min

(2 marks)

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Question A3.

The rate constant for a particular reaction was measured to be 0.142 L mol–1 s–1 at 1127 ºC and
0.693 L mol–1 s–1 at 1227 ºC

Which one of the following is the activation energy closest to for this reaction?

A. 6.4 x 104 J mol–1

B. 1.3 x 101 J mol–1

C. 9.5 x 103 J mol–1

D. 3.3 x 104 J mol–1

E. 2.8 x 105 J mol–1 (2 marks)

The following diagram is required to answer questions A4-A9

Question A4.

What is the relationship between structures 1 and 3?

A. Conformational Isomers

B. Enantiomers

C. Diastereomers

D. Cis-trans isomers
E. Constitutional isomers
(2 marks)

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CHEM10006 Mock Exam 3

Question A5.

What is the relationship between structures 1 and 9?

A. Conformational Isomers

B. Enantiomers

C. Diastereomers

D. Cis-trans isomers

E. Constitutional isomers (3 marks)

Question A6.
What is the relationship between structures 5 and 6?

A. Conformational Isomers

B. Enantiomers

C. Diastereomers

D. Cis-trans isomers

E. Constitutional isomers (3 marks)

Question A7.

What is the relationship between structures 3 and 11?

A. Conformational Isomers

B. Enantiomers

C. Diastereomers

D. Cis-trans isomers

E. Constitutional isomers (3 marks)

Question A8.

How many possible stereoisomers exist for structure 2?

A. 2 B. 3 C. 4 D. 5 E. 6
(2 marks)

Question A9.

Which of the isomeric structures (1, 3, 7 or 11) represents the (2S,3R)–configuration?

A. 1 B. 3 C. 7 D. 11

(2 marks)

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Question A10.

Which of the following E, Z designations for the molecules below are CORRECT?

A. II and III only

B. I, II, III and V only

C. I and IV only

D. V only

E. II, III and IV only (2 marks)

The following diagram is required to answer questions A10-A14

Question A11.

How many sp3 hybridised carbon atoms are present in the molecule above?

A. 2 B. 3 C. 4 D. 6 E. 7
(2 marks)

Question A12.

How many sp3 hybridised nitrogen atoms are present in the molecule above?

A. 0 B. 1 C. 2 D. 3 E. 4
(2 marks)

Question A13.

Which of the following is the correct stereochemical descriptor for the carbon atom labelled
with an asterisk ( * )in the molecule?

A. E B. Z C. (-) D. R E. S
(2 marks)
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CHEM10006 Mock Exam 3

Question A14.
How many -electrons are involved in formation of the aromatic functional group within this
molecule?

A. 4 B. 6 C. 8 D. 10 E. This molecule
is not aromatic.
(3 marks)

Question A15.

In the lowest energy chair conformation of the cyclohexane containing molecule shown below,
how many of the substituents will be axial?

A. 0 B. 1 C. 2 D. 3 E. 6.

(3 marks)

Question A16.

What is the major product expected from the following reaction?

A. B. C.

D. E.

(2 marks)

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Question A17.

Which of the following reactions is an SN2 reaction?

A. I only

B. III only

C. I and III only

D. I and IV only

E. II only

(2 marks)

Question A18.

Which one of the following aldohexose structures will cyclise to form the pyranose chair
conformation shown below?

A. B. C. D.
(2 marks)

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CHEM10006 Mock Exam 3

Question A19.

Which one of the following statements about the disaccharide structure shown below is
correct?

A. The disaccharide is a reducing sugar containing an α-1,4-glycosidic linkage.

B. The disaccharide is a reducing sugar containing an α-1,2-glycosidic linkage.

C. The disaccharide is a non-reducing sugar containing an α-1,4-glycosidic linkage

D. The disaccharide is a reducing sugar containing a β-1,4-glycosidic linkage

E. The disaccharide is a non-reducing sugar containing a β-1,4- glycosidic linkage.

(3 marks)

Question A20.

Which of the following statements about DNA is correct?

I. Nucleosides are formed from nucleotides by phosphorylation.

II. Adenine and Guanine are types of heterocyclic bases called pyrimidines.

III. Base pairing can occur between the keto forms of hypoxanthine and thymine.

IV. Base pairing can occur between the keto form of guanine and the imino form of
cytosine.
A. I and III only

B. II and IV only

C. II, III and IV only

D. I, II, III, and IV

E. None of the statements are correct.

(2 marks)

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Question A21.

Which of the following chemical equations does NOT correspond to a standard molar enthalpy
of formation 25°C?

A. CO2 (g) →C(s) + O2(g)

B. N2(g) + 2O2(g) → N2O4(g)

C. Ca(s) + C(s) + 3/2O2(g) → CaCO3(s)

D. S(s) + 3/2O2(g) → SO3(g)

E. 2C(s) + 3H2(g) + ½O2(g) → CH3OCH3(g)

(2 marks)

Question A22.

A gas phase reaction reaction is exothermic and leads to atoms being distributed among fewer
molecules in the products than in the reactants. Will the reaction be spontaneous?

A. The reaction will always be spontaneous.

B. The reaction will be spontaneous if TΔrS° > ΔrH°.
C. The reaction will be spontaneous if TΔrS° < ΔrH°
D. The reaction will never be spontaneous.
E. There is not enough information to tell if the reaction will be spontaneous or not

(2 marks)

Question A23.
Which of the following would result in a decrease in the entropy of the system?
I. 2H2(g) + O2(g) 2H2O(l)
II. CO(g) + 2H2(g) CH3OH(g)
III. Compressing 0.5 mol Argon gas at a constant temperature from 2.0 L to 1.5 L.
IV. Heating 1 mol of gas is at a constant volume from 298 K to 373K
A. I and II only

B. I, II and III only

C. I, II, III and IV only

D. I and III only

E. I, II, IV only
(2 marks)

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CHEM10006 Mock Exam 3

Question A24.
For a certain reaction, the value of the equilibrium constant at 25.0 °C is 3.9, and the value of the
equilibrium constant at 100.0 °C is 3.4 x 10-3. Which one of the following is the closest value of
the enthalpy for the reaction, assuming this value remains constant in the temperature range
studied?

A. 8.69 x 104 kJ mol–1

B. 86.9 kJ mol–1

C. –86.9 kJ mol–1

D. –8.69 x 104 kJ mol–1

E. 869 kJ mol–1
(2 marks)

Question A25.
Consider the following reaction which has reached equilibrium:
NH4NO3(s) ⇌ N2O(g) + 2H2O(g) ΔH = −366 kJ mol−1
Which of the following changes would shift the equilibrium to the right?
I. Increase the temperature.
II. Remove H2O.
III. Increase the volume of the container.
IV. Add more N2O.

A. II and III only

B. I, II, and II only
C. I, II, III and IV only
D. II, III and IV and
E. II only (2 marks)

Question A26.
The compound methylamine, CH3NH2, has a Kb value of 4.4 x 10–4.

The pH of 100 mL of a 0.200 M aqueous solution of methylamine will be closest to?

A. 12.0 B. 10.6 C. 10.0 D. 2.2 E. 11.5

(2 marks)

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Question A27.

Histidine is an amino acid, which dissociates as follows:

Based on this information, the isoionic (isoelectric) point, pI of histidine is closest to:
A. 3.9 B. 7.7 C. 7.0 D. 5.6 E. 4.3
(2 marks)

Question A28.

HEPES (4-(2-hydroxyethyl)-1-piperazineethanesulfonic acid) undergoes the following acid-

base reaction:

The pH of a solution prepared by dissolving 0.02 moles HEPES in water to a final volume of
100 mL is closest to:

A. 4.1 B. 9.9 C. 10.4 D. 3.7 E. 11.8

(3 marks)

Question A29.
At 25 °C Henry’s Law constant for phosphine (PH3) gas in water is 8.1 x 10-3 M atm–1. Calculate
the mass (in grams) of PH3 gas that can be dissolved in 1200 mL of water at 25 °C and a PH3
partial pressure of 1.90 atm.

A. 18.5 g B. 0.63 g C. 0.018 g D. 6.3 g E. 12.6 g

(3 marks)

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CHEM10006 Mock Exam 3

Question A30.

Consider the following electrochemical cell:

Zn(s)|Zn2+(aq) || Cd2+(aq)|Cd(s)

Calculate the Ecell when [Zn2+]=0.02 M and [Cd2+]=0.4 M.

A. 0.80 V B. 0.44 V C. 0.28 V D. 0.32 V E. 0.40

(2 marks)

Question A31.

Which of the following complexes/complex ions can exist as geometric isomers?

Note: en = ethylenediamine (NH2CH2CH2NH2).

I. Ni(NH3)2Cl2 (square planar)

II. [Ni(CN)4]2– (square planar)

III. [Co(en)3]3+ (octahedral)

IV. [Co(en)2Cl2]+ (octahedral)

A. I only

B. III and IV only

C. I and IV only

D. I, III, IV only

E. I, II, III and IV only (2 marks)

Question A32.

Consider the following amino acids

I. Aspartic acid (Asp)

II. Leucine (Leu)
III. Histidine (His)
IV. Tyrosine (Tyr)
Which of the above amino acids are likely to bind to a metal centre through their sidechains as
monodentate ligands?
A. II only
B. III and IV only
C. I, III and IV only
D. II, III, and IV only
E. I, II, III and IV only
(2 marks)

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Question A33.

The following species are some of the components of the biogeochemical cycle of sulfur:

SO32–, S4, H2S, FeS

The oxidation states of sulfur in these species are:

SO32– S4 H2S FeS
A. 4+ 0 2– 2–
B. 3+ 0 2– 3–
C. 4+ 0 2– 3–
D. 3+ 0 2– 2–
E 4+ 0 3– 3–

(2 marks)

Question A34.

Which of the following ions has a [Ar]d5 electron configuration?

A. Cr3+ B. Ni2+ C. Co2+ D. Fe3+ E. Zn3+

(2 marks)

Question A35.

The tertiary structure of a protein describes its:

A. Amino acid sequence.

B. Oligomeric structure.

C. Overall structure/fold in three dimensions.

D. Structural composition in terms of alpha helices, beta sheets, loops.

(2 marks)

Question A36.

Which of the following properties correctly describes cell (phospholipid) membranes?

A. hydrophobic throughout

B. positively charged at the membrane surface; hydrophobic core

C. negatively charged at the membrane surface; positively charged core

D. negatively charged at the membrane surface; hydrophobic core

(2 marks)
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CHEM10006 Mock Exam 3

Question A37.

Consider the concentration cell depicted below in which the right-hand side compartment is the
cathode.

If Ecell was measured to be 16.5 mV for the cell above, what is the [Zn2+] in the left hand-side
compartment?

A. 0.26 M B. 0.50 M C. 3.5 M D. 1.8 M E. 0.76 V

(2 marks)

Question A38.

Adenosine triphosphate (ATP) is described as the ‘energy currency of the cell’. Under
physiological conditions, ATP is:

A. Is an ion with an overall charge of –3

B. A zwitterion.
C. Is an ion with an overall charge of –2
D. Is a neutral molecule

E. Is an ion with an overall charge of –4

(2 marks)

Question A39.
Bleach contains 10% of the active ingredient NaOCl. The percentage by mass of sodium in
NaOCl is:

A. 3% B. 10% C. 3% D. 69 E. 31%

(2 marks)

Question A40.

Calculate the boiling point elevation of an aqueous solution of 0.029 m glucose.

Note: Kb for glucose is 0.512 C m-1.

A. 0.015 C B. 0.13 C C. 0.044 C D. 0.030 C E. 0.79 C

(2 marks)

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Question A41.

Calculate the value of x:

10x = 1757688

A. 6.05 B. 51.5 C. 111.4 D. 6.24 F. 77.9

(2 marks)

****END OF SECTION A****

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CHEM10006 Mock Exam 3

Chemistry for Biomedicine: Mock Examination 1

SECTION B

A table of selected physical constants, useful quantities and conversion factors is provided in
Appendix 1, structures of nucleobases in Appendix 2, structures of the 20 common amino
acids in Appendix 3 and the D-aldohexose "family tree" in Appendix 4.

Students are advised to answer ALL Questions, B1 to B10:

Question 1. (10 marks)

During a practical experiment, a student in the laboratory was measuring the change in
concentration of N2O5 for the reaction below at two different temperatures. The following
data was collected.
2N2O5(g) → 4NO2(g) + O2(g)

Experiment 1: Experiment 2
Temp = 338 K Temp = ?? K
Time (s) [N2O5] [N2O5]

0 1.0 x 10–1 M 1.0 x 10–1 M

100 6.14 x 10–2 M 9.54 x 10–2 M

300 2.33 x 10–2 M 8.63 x 10–2 M

600 5.41 x 10–3 M 7.43 x 10–2 M

900 1.26 x 10-3 M 6.39 x 10–2 M

(a) For both Experiments 1 and 2, calculate the average rate of consumption of N2O5
between 0 and 100 seconds.

(b) For Experiment 2, the student forgot to record the temperature at which the reaction
was run. Compared to Experiment 1, was the reaction run at a higher or lower
temperature. Justify your answer.

(c) Using the data given in the table, what is the overall order for the reaction:

2N2O5(g) → 4NO2(g) + O2(g)

Justify your answer. Show all your working out.

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CHEM10006 Mock exam 3

Question 2. (8 marks)

(a) Draw the staggered Newman projections for the aldotetrose molecule (shown
below) looking down the C2 – C3 bond. Identify which one is the most stable
conformation.

(b) What is the stereochemistry at each of the asymmetric centres in the aldotetrose
molecule shown above?

Question 3. (9 marks)

Catalytic hydrogenation follows a syn addition pathway, i.e., the two hydrogen atoms are
added to an alkene double bond on the same side, as shown below for 2,3-dimethylbutene.
Draw all the reaction products formed by hydrogenation of the Z and E isomers of 2,3-
dichlorobutene, and assign the absolute configurations to each chiral centre.

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 CHEM10006 Mock Exam 3

Question 4. (12 marks)

Consider the disubstituted cyclohexanes A and B below. Cyclohexane A reacts via a

neighbouring group reaction (step 1) to form an intermediate C, which then reacts with
sodium acetate (step 2) to form cyclohexane B. The structures of the acetyl (Ac) and
tosyl (Ts) groups are shown in the boxes.

Mechanism A

(a) What is the relationship between the substituents in cyclohexane A?

What is the relationship between the substituents in cyclohexane B?

(b) Why does the tosylate act as the leaving group?

(c) Draw the most stable cyclohexane chair configuration of cyclohexane A.

(d) Draw the higher energy cyclohexane chair configuration obtained, when the chair
conformation drawn in part (c) above undergoes a ringflip.
Now add the curly headed arrows (a) and (b) (as seen in Mechanism A) to
show how the neighbouring group reaction occurs.

(e) Briefly explain why the conversion of cyclohexane A to B proceeds with retention of
configuration.

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CHEM10006 Mock exam 3

Question 5. (4 marks)

Draw structures for the nucleophilic substitution products (a) and (b), that would be
produced in the reaction scheme shown below.

Question 6. (4 marks)

Draw the Fischer projection for the aldopentose shown below.

Question 7. (5 marks)

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CHEM10006 Mock Exam 3

Partial acid hydrolysis of a peptide resulted in the following fragments. Assemble these
fragments to determine the sequence of the peptide.

Fragments:

SIME VAGD ERY NIVA

GDIE RTSIM EHC RYRT

Question 8. (10 marks)

The hydrolysis of sucrose to glucose follows the reaction below and has an enthalpy of
reaction of -41.5 kJ mol–1. The hydrolysis reaction is given below:

C12H22O11(aq) + H2O(l) ⇌ 2C6H12O6(aq)

(a) Calculate the enthalpy of formation of sucrose, given the following data. You will be
awarded marks for working out. Not just the answer.
Substance fH kJ mol–1 (at 25C) S J K–1 mol–1 (at 25C)
C12H22O11(aq) ?? 360.24
H2O(l) –285.9 69.95
C6H22O11 –1274.4 212.1

(b) Using the thermodynamical data above, calculate the equilibrium constant for the
hydrolysis of sucrose at 25 ºC? Show all your working out.

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CHEM10006 Mock exam 3

Question 9. (12 marks)

For each of these species below:

A. B. C. D.

CO32– SO3 HCN HOCO

• draw a Lewis structure (include lone pairs where required)

• show formal charges where required
• predict the molecular shape
• indicate if the species is a radical
• indicate the molecule is polar or non-polar
• show any resonance structures if applicable

Question 10. (3 marks)

EDTA4–, a hexadentate ligand, is most effective at chelating with metal ions when the pH
is greater than 12. Explain why the chelating ability of the ligand decreases at lower pH
levels.

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CHEM10006 Mock Exam 3

Question 11. (6 marks)

Calculate the solubility of zinc carbonate (Ksp = 1.5 x10–10) when placed in:

(a) water

(b) 0.050 M K2CO3

Show all working out.

Question 12. (7 marks)

Plasticyanin is a blue copper protein, which functions in photosynthesis.

(a) Which metal binds to plastocyanin?

(b) Draw the metal binding site of plastocyanin showing the ligating amino acid side chains
(label each side chain).

(c) The metal binding site causes the protein to have what colour in the oxidised state?

(d) What is meant by ‘entatic’ state when explaining the redox properties of plastocyanin?

****END OF PAPER****

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CHEM10006 Mock exam 3

APPENDIX 1.
Selected physical constants, useful quantities and conversion factors.

Avogadro constant (NA) 6.0221  1023 mol-1

1 Atomic mass unit (u) 1.6605  10-27 kg

8.314 J K-1 mol-1

Gas constant (R)
or 0.08206 L atm K-1 mol-1

Speed of light (c) 2.9979  108 m s-1

Planck constant (h) 6.6261  10-34 J s photon-1
Rydberg constant ( ) 3.29  1015 Hz
Mass of an electron (me) 9.109  10-31 kg
Bohr radius (ao) 53 pm
1 Atmosphere (atm) 101 325 Pa = 760 mm Hg
1 Bar 100 kPa = 0.987 atm
Faraday constant (F) 9.6485  104 C mol-1
RT/F (at 298 K) 0.0257 V
2.303 RT/F (at 298 K) 0.0592 V
Absolute zero, 0 K -273.15 °C
Specific heat of water 4.18 J g-1 ºC-1

Molar Masses Selected Standard Reduction Potentials

Element M/g mol-1
H 1.008
Half Reaction E° / V
He 4.00
C 12.01 O2 + 4H+ + 4e- → 2H2O 1.23 V
N 14.01 I2 + 2e- → 2I- 0.54 V
O 16.00
Na 22.99 Cu2+ + 2e- → Cu 0.34 V
Mg 24.31 2H+ + 2e- → H2 0.00 V
S 32.07
Cl 35.45 Cd2+ + 2e- → Cd -0.40 V
Ca 40.08 Zn2+ + 2e- → Zn -0.76 V
Cu 63.55
I 126.90 2H2O + 2e- → H2 + OH- -0.83 V
Pu 244.00 Mg2+ + 2e- → Mg -2.37 V

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CHEM10006 Mock Exam 3

APPENDIX 2: STRUCTURES OF THE NUCLEOBASES

APPENDIX 3: STRUCTURES OF THE 20 COMMON AMINO ACIDS

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CHEM10006 Mock exam 3

APPENDIX 4: THE D-ALDOHEXOSE “FAMILY TREE”

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