2010 CHEM EXAM 1 2

SECTION A continued
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The following information refers to Questions 1 and 2.
The following titration curve was obtained by measuring the pH in a reaction ask during an acid-base titration.
0
2
4
6
8
10
12
14
20
volume (mL)
pH
Question 1
The graph represents the change in pH in the reaction ask when
A. a weak acid is added to a strong base.
B. a weak base is added to a strong acid.
C. a strong acid is added to a weak base.
D. a strong base is added to a weak acid.
Question 2
Which one of the following is a suitable indicator for use in this titration?
A. phenol red
B. thymol blue
C. phenolphthalein
D. bromophenol blue
SECTION A Multiple-choice questions
Instructions for Section A
Answer all questions in pencil on the answer sheet provided for multiple-choice questions.
Choose the response that is correct or that best answers the question.
A correct answer scores 1, an incorrect answer scores 0.
Marks will not be deducted for incorrect answers.
No marks will be given if more than one answer is completed for any question.
3 2010 CHEM EXAM 1
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Question 3
A sample of the insecticide dichlorodiphenyltrichloroethane (DDT), C
14
H
9
Cl
5
, was found to contain 0.120 g
of carbon.
What mass of chlorine was present in the sample?
A. 0.127 g
B. 0.355 g
C. 0.994 g
D. 1.01 g
Question 4
When 1.0 mole of Cu
3
FeS
3
and 1.0 mole of O
2
are mixed and allowed to react according to the equation
2Cu
3
FeS
3
(s) + 7O
2
(g) 6Cu(s) + 2FeO(s) + 6SO
2
(g)
A. no reagent is in excess.
B. 5 mole of O
2
is in excess.
C.
5
7
mole of Cu
3
FeS
3
is in excess.
D.
2
7
mole of Cu
3
FeS
3
is in excess.
Question 5
One possible reaction that occurs when trinitrotoluene (TNT), C
7
H
5
N
3
O
6
, explodes is
2C
7
H
5
N
3
O
6
(s) 2C(s) + 12CO(g) + 5H
2
(g) + 3N
2
(g)
When one mole of TNT explodes the total volume of the gases produced from this reaction, measured at 27 C and
1.00 10
2
kPa, is closest to
A. 0.249 L
B. 22.7 L
C. 249 L
D. 274 L
2010 CHEM EXAM 1 4
SECTION A continued
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Question 6
Consider the following TLC plate of compounds X, Y and Z developed using a suitable mobile phase on a polar
stationary phase.
solvent front
origin
X Y Z
3.20
2.75
2.15
1.70
0.80
0.00
scale
(cm)
The R
f
value of the most polar component in this TLC separation is
A. 0.29
B. 0.62
C. 0.78
D. 0.80
Question 7
Which of the following would be the most suitable analytical technique to determine the ratio of
235
U to
238
U in a
sample of uranium metal?
A. mass spectroscopy
B. gas liquid chromatography
C. atomic absorption spectroscopy
D. nuclear magnetic resonance spectroscopy
Question 8
When a sample absorbs infrared radiation
A. covalent bonds are broken.
B. covalent bonds stretch and vibrate.
C. the spin alignment of certain nuclei changes.
D. electrons in atoms move to higher energy levels.
5 2010 CHEM EXAM 1
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Question 9
The graph shows the absorption spectra of three food dyes: Blue No. 1, Red No. 2 and Yellow No. 4.
0
0.2
0.4
0.6
0.8
1.0
400 500 600 700
wavelength (nm)
Yellow No. 4
Red No. 2
Blue No. 1
absorbance
Which one of the following is the best wavelength to determine the concentration of Red No. 2 dye in a solution
containing a mixture of all three dyes?
A. 430 nm
B. 500 nm
C. 540 nm
D. 620 nm
Question 10
What is the correct systematic name for the following compound?
H
3
C CH CH CH
3
CH
2
CH
3
CH
2
CH
3
A. 2-ethyl-3-methylpentane
B. 3-methyl-4-ethylpentane
C. 3,4-dimethylhexane
D. 2,3-diethylbutane
2010 CHEM EXAM 1 6
SECTION A continued
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Question 11
For which one of the following molecular formulas is there only one possible structure?
A. C
2
HCl
3
B. C
2
H
4
Cl
2
C. C
2
H
2
Cl
2
D. C
4
H
9
OH
Question 12
An organic compound reacts with both dilute hydrochloric acid and dilute sodium hydroxide solution.
The compound could be
A. C
3
H
7
Cl
B. C
3
H
7
NH
2
C. C
4
H
9
COOH
D. H
2
NCH
2
COOH
Question 13
Which one of the following organic reactions does not result in the product shown on the right-hand side of the reaction?
A.
H C
H
H
H
H
H
H
H
H
C
C
C Cl
H C
H
H
H
H
H
H
H
H
C
C
C O
H
H
H
H C
NaOH
B.
H C
H
H
H
H
H
H
H C
C
C
H
H
HCl
C.
O
C
C
O
H
+
D.
H C
H
H
H
H
H
C
C
H C
H
H
O
H
H
H
C
C H
H
2
O, H
+
H C
H
H
H
H
H
CH
3
OH +
O
C
O
H
H C
H
H
H
H
C
C
C
H
H
Cl
H
7 2010 CHEM EXAM 1
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Question 14
The side chains of some amino acids are able to form amide (peptide) bonds. Glutathione is a tripeptide that protects
cells in humans by acting as an antioxidant. The structure of glutathione is
H
2
N C CH
2
CH
2
C C C C N CH
2

OH
C
SH
CH
2
O

The molecule of glutathione contains residues from the amino acids cysteine and glycine.
The name of the third amino acid found in glutathione is
A. asparagine.
B. aspartic acid.
C. glutamine.
D. glutamic acid.
Questions 15 and 16 refer to the following information.
The following diagram is a simplied illustration of the protein insulin. Insulin consists of 51 amino acids arranged in
two individual chains linked by disulde bridges.
S S
S
S
S
S
Question 15
How many peptide links are present in one molecule of insulin?
A. 48
B. 49
C. 50
D. 51
Question 16
Disulde bridges are formed when the side chains of two amino acid residues react.
The pair of amino acids that form the disulde bridges could be
A. cysteine and serine.
B. cysteine and glycine.
C. cysteine and cysteine.
D. cysteine and glutamic acid.
2010 CHEM EXAM 1 8
SECTION A continued
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Question 17
The following are incomplete and unbalanced equations representing three types of chemical reactions that
involve glucose. In reactions 1 and 3, product A is the same compound. In reactions 2 and 3, product B is the same
compound.
reaction 1 C
6
H
12
O
6
(aq) C
2
H
5
OH(aq) + product A
reaction 2 C
6
H
12
O
6
(aq) C
12
H
22
O
11
(aq) + product B
reaction 3 C
6
H
12
O
6
(aq) product A + product B
Which one of the following correctly names reaction 3 and identies product A and product B?
Reaction 3 Product A Product B
A. fermentation water carbon dioxide
B. fermentation carbon dioxide water
C. combustion water carbon dioxide
D. combustion carbon dioxide water
Question 18
The structure of oxalic acid is shown below.
O
O
O
O H H
C C
A 25.0 mL solution of oxalic acid reacts completely with 15.0 mL of 2.50 M NaOH.
The concentration of the oxalic acid solution is
A. 0.667 M
B. 0.750 M
C. 1.33 M
D. 1.50 M
9 2010 CHEM EXAM 1
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Question 19
The structure of Tamiu

, an antiu drug, is shown below.

CH
3
C
O
O
CH
CH
2
H
3
C
C
H
3
C
N
H
NH
2
C
O O
CH
2
H
3
C
I
II
III
H
H
The names of the functional groups labelled I, II and III are
I II III
A. amide amino carboxylic acid
B. amino amide ester
C. amide amino ester
D. amino amide carboxylic acid
Question 20
Copolymers are obtained when two or more different monomers are allowed to polymerise together.
Part of a copolymer chain is shown below.
CH
3
C
H
CH
3
C
H
H
C
H
CH
3
C
H
CH
3
C
H
CH
3
C
H
CH
3
C
H
H
C
H
CH
3
C
H
CH
3
C
H
CH
3
C
H
The two alkenes that could react together to form this polymer are
A. propene and but-1-ene.
B. propene and but-2-ene.
C. but-1-ene and but-2-ene.
D. pent-2-ene and but-2-ene.
END OF SECTION A
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2010 CHEM EXAM 1 10
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Question 1
The amount of iron in a newly developed, heat-resistant aluminium alloy is to be determined.
An 80.50 g sample of alloy is dissolved in concentrated hydrochloric acid and the iron atoms are converted to Fe
2+
(aq)
ions.
This solution is accurately transferred to a 250.0 mL volumetric ask and made up to the mark.
20.00 mL aliquots of this solution are then titrated against a standard 0.0400 M potassium permanganate solution.
5Fe
2+
(aq) + MnO
4

(aq) + 8H
+
(aq) 5Fe
3+
(aq) + Mn
2+
(aq) + 4H
2
O(l)
Four titrations were carried out and the volumes of potassium permanganate solution used were recorded in the table
below.
Titration number 1 2 3 4
Volume of KMnO
4
(mL) 22.03 20.25 21.97 21.99
a. Write a balanced half-equation, including states, for the conversion of MnO
4

ions, in an acidic solution,

to Mn
2+
ions.
2 marks
b. Calculate the average volume, in mL, of the concordant titres of the potassium permanganate solution.
1 mark
SECTION B Short answer questions
Instructions for Section B
Answer all questions in the spaces provided in blue or black pen or pencil.
To obtain full marks for your responses you should
give simplied answers with an appropriate number of signicant gures to all numerical questions; unsimplied
answers will not be given full marks.
show all working in your answers to numerical questions. No credit will be given for an incorrect answer unless
it is accompanied by details of the working.
make sure chemical equations are balanced and that the formulas for individual substances include an indication
of state; for example, H
2
(g); NaCl(s)
SECTION B Question 1 continued
11 2010 CHEM EXAM 1
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SECTION B continued
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c. Use your answer to part b. to calculate the amount, in mol, of MnO
4

(aq) ions used in this titration.

1 mark
d. Calculate the amount, in mol, of Fe
2+
(aq) ions present in the 250.0 mL volumetric ask.
2 marks
e. Calculate the percentage, by mass, of iron in the 80.50 g sample of alloy. Express your answer to the correct number
of signicant gures.
3 marks
Total 9 marks
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SECTION B Question 2 continued
Question 2
The molecular formula of an unknown compound, X, is C
3
H
6
O
2
.
The infrared
13
C NMR and
1
H NMR spectra of this compound are shown below.
0.8
0.4
A
infrared spectrum
3000 2000 1000
wave number (cm
1
)
transmittance
13
C NMR
160 140 120 100 80 60
TMS
calibration
peak
40 20 0
ppm
1
H NMR
8 9 10 7 6 5 4 3 2
TMS
calibration
peak
1 0
ppm
13 2010 CHEM EXAM 1
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SECTION B continued
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The
1
H NMR spectrum data is summarised in the following table.
Chemical shift (ppm) Relative peak area Peak splitting
1.3 3 triplet (3)
4.2 2 quartet (4)
9.0 1 singlet (1)
a. Using the Infrared absorption data on page 7 of the Data Book, identify the atoms and the bonds between them
that are associated with the absorption labelled A on the infrared spectrum.
1 mark
b. How many different carbon environments are present in compound X?
1 mark
c. How many different hydrogen environments are present in compound X?
1 mark
d. i. The signal at 1.3 ppm is split into a triplet. What is the number of equivalent protons bonded to the adjacent
carbon atom?
ii. Draw the grouping of atoms that would give rise to the triplet and quartet splitting patterns.
1 + 1 = 2 marks
e. A chemical test showed that compound X does not react with a base.
Propose a structure for compound X that is consistent with all the evidence provided.
2 marks
Total 7 marks
2010 CHEM EXAM 1 14
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SECTION B continued
Question 3
The molecules ethanol and nitrogen dioxide have the same molar mass (M = 46 g mol
1
). They can be easily distinguished
by mass spectrometry.
The mass spectra of the two molecules are shown below.
100
80
60
40
20
0
10 20 30 40 50
relative
abundance
relative
abundance
mass spectrum
m/z
100
80
60
40
20
0
10 20 30 40 50
mass spectrum
m/z
Spectrum A
Spectrum
a. Write an equation showing how either an ethanol molecule or a nitrogen dioxide molecule becomes ionised in the
mass spectrometer.
1 mark
b. Which mass spectrum cannot be that of nitrogen dioxide? What evidence does the mass spectrum provide to
support your answer?
2 marks
c. What is the formula of the species that produces the peak seen at m/z 30 in spectrum B?
1 mark
Total 4 marks
15 2010 CHEM EXAM 1
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SECTION B continued
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Question 4
A single strand of DNA consists of a long chain of monomers called nucleotides. The structure of one of these nucleotides
of DNA is shown below.
Each nucleotide will polymerise with other nucleotides to form a single strand of DNA.
Part of this nucleotide will also form bonds with a complementary nucleotide on a parallel strand of DNA forming the
double helix structure.
H
3
C
O
NH
O N
O
O

O
OH
P
OH
CH
2
O
A
D
B
E
F
C
a. Circle only the letters which represent the sites where this nucleotide can form bonds with other nucleotides to
form a single strand of DNA.
A B C D E F
2 marks
b. i. Name the type of bonding that holds the two strands in human DNA together.
ii. Circle only the letters that represent the locations where these bonds between the two strands of DNA are
formed.
A B C D E F
1 + 2 = 3 marks
Total 5 marks
2010 CHEM EXAM 1 16
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SECTION B Question 5 continued
Question 5
A forensic chemist wants to test the accuracy of a gas chromatograph that is to be used for the analysis of blood alcohol
content.
A blood sample may contain a number of volatile chemicals that can interfere with the identication and measurement
of ethanol in the blood. A sample containing a mixture of ethanol and several other volatile chemicals was injected into
the gas chromatograph. The following chromatogram was obtained.
m
e
t
h
a
n
o
l
a
c
e
t
a
l
d
e
h
y
d
e
e
t
h
a
n
o
l
p
r
o
p
a
n
-
2
-
o
l
a
c
e
t
o
n
e
p
r
o
p
a
n
-
1
-
o
l
0.0 0.1 0.2 0.3 0.4 0.5 0.6 0.7 0.8 0.9 1.0 1.1 1.2 1.3 1.4 1.5 1.6 1.7 1.8 1.9 2.0 2.1 2.2 2.3 2.4
20
40
60
80
100
retention time (minutes)
recorder
response
a. The forensic chemist claims that the presence of these volatile chemicals would not affect the qualitative analysis
of ethanol.
i. What evidence is presented in the chromatogram to support this claim?
ii. To determine the percentage of alcohol in a blood sample only the peak at a retention time of 0.9 minutes is
measured. Explain why.
1 + 1 = 2 marks
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SECTION B continued
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The following calibration graph was constructed using simulated standard blood alcohol samples ranging in concentration
from 0.000% to 0.400% m/v ethanol. Each standard was run through the chromatography column and the area under
the peak produced at a retention time of 0.9 minutes was measured.
250 000
200 000
150 000
100 000
50 000
0
0.000 0.100 0.200 0.300 0.400 0.500
% ethanol (m/v)
peak area
The blood alcohol content of a car driver was determined using this chromatographic technique.
b. Determine the percentage (m/v) of alcohol in the drivers blood if the peak area at a retention time of 0.9 minutes
was found to be 110 000.
1 mark
Total 3 marks
2010 CHEM EXAM 1 18
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SECTION B Question 6 continued
Question 6
Enzymes are complex protein structures that function as biological catalysts.
a. Why does a particular enzyme generally only catalyse a specic reaction?
1 mark
Invertase is an enzyme which catalyses the conversion of sucrose to glucose and fructose. Invertase has a maximum
activity temperature different from many other enzymes. The graph below shows the results of a study into the effects
of both pH and temperature on the activity of invertase in sucrose solution.
35 C
45 C
55 C
65 C
activity of invertase vs pH at different temperatures (C)
2 3 4 5 6 7 8
0
50
100
150
200
250
300
350
400
450
pH
activity
(mmol glucose/
mg invertase)
in 30 minutes
temperature
b. At what temperature and pH does the enzyme in the study have maximum activity?
Temperature __________ pH __________
2 marks
c. Why does changing the pH from the optimum value cause a decrease in the activity of the enzyme?
1 mark
19 2010 CHEM EXAM 1
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SECTION B continued
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d. In this study the activity of the enzyme was measured as the number of millimole of glucose produced per milligram
of enzyme (mmol glucose/mg invertase) in 30 minutes.
Assuming excess sucrose, calculate the mass of glucose (M
r
= 180) produced in 30 minutes from a sucrose solution
containing 1.00 10
4
g of invertase if the measured activity is 300 mmol glucose/mg invertase.
2 marks
Total 6 marks
2010 CHEM EXAM 1 20
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SECTION B Question 7 continued
Question 7
a. Biodiesel is an alternative to standard diesel fuel. Biodiesel is made from biological ingredients instead of petroleum.
Biodiesel is usually made from plant oils or animal fats through a series of chemical reactions.
In one process a common triglyceride in palm oil, known as POP, is reacted with methanol in the presence of
potassium hydroxide as a catalyst. The result is a mixture of methyl esters of the fatty acids (biodiesel).
i. The value of the stoichiometric ratio
number of moles of methanol
number of moles of POP
is
ii. Calculate the volume, in litres, of methanol (density = 0.79 g mL
1
) required to react completely with 10.0 kg
of the triglyceride POP (M
r
= 833) to produce glycerol and the mixture of methyl esters.
1 + 3 = 4 marks
21 2010 CHEM EXAM 1
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SECTION B continued
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b. Cervonic acid is a polyunsaturated fatty acid found in sh oil. The number of carbon-carbon double bonds in a
molecule of cervonic acid can be determined by titration with iodine, I
2
, solution. An addition reaction takes place
between the double bonds in cervonic acid and iodine.
20.00 mL of 0.300 M I
2
solution reacted exactly with 0.328 g of cervonic acid. The molar mass of cervonic acid
is 328.0 g mol
1
.
i. Calculate the number of double bonds in a molecule of cervonic acid.
There are 22 carbon atoms in a molecule of cervonic acid.
ii. What is the formula of cervonic acid?
3 + 1 = 4 marks
Total 8 marks
2010 CHEM EXAM 1 22
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SECTION B Question 8 continued
Question 8
Since ancient times, the bark of willow trees has been used for pain relief. In the 19th century, chemists isolated the active
compound, salicin, from the bark. This was eventually converted into aspirin, which is now a widely used drug.
The reaction scheme below shows the steps used to carry out the conversion.
C
OH
OH

C
OH
O

C CH
3
aspirin
step 3
step 2
H
2
SO
4
CH
2
OH
H
HO
H OH
H
O
O
OH
H
CH
2
OH
CH
2
OH
OH
salicyl alcohol
CH
2
OH
H
HO
H OH
H
O
OH
H
A
+
step 1
salicin
H
H
a. What type of linkage is circled in the structure of salicin?
1 mark
b. In step 1, salicyl alcohol and another compound is produced.
i. What group of biomolecules does this other compound belong to?
ii. The structure of this other compound is not complete. Write the formula of the atom or group of atoms
represented by A in the reaction scheme above.
1 + 1 = 2 marks
c. Step 2 involves the conversion of salicyl alcohol into salicylic acid.
i. What type of reaction is step 2?
ii. Suggest a suitable reagent to carry out the reaction.
1 + 1 = 2 marks
d. Step 3 requires sulfuric acid catalyst and another reagent. Name this reagent.
1 mark
23 2010 CHEM EXAM 1
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SECTION B continued
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e. Aspirin reacts with a strong base according to the equation
C
OH
O

C CH
3
+ OH

(aq) H
2
O(l) + product B
Draw the structure of product B.
1 mark
Total 7 marks
2010 CHEM EXAM 1 24
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Question 9
The boiling points of several alkanols are provided in the following table.
Alkanol methanol ethanol propan-1-ol butan-1-ol pentan-1-ol
Boiling point (C) 64.5 78.3 97.2 117.2 138.0
A mixture of two of these alkanols is to be separated in an experiment using fractional distillation. The mixture is placed
into the distillation apparatus at room temperature and then gently heated. The rst fraction is collected at 97.2 C.
a. i. Identify one alkanol that could not be present in this mixture.
ii. By specically referring to this experiment, explain why the alkanol identied in part i. could not be
present.
1 + 1 = 2 marks
b. Provide one reason why the distillation ask should not be heated using a bunsen burner.
1 mark
c. Butane and propan-1-ol have similar molar masses. The boiling point of butane is 138.4 C and that of
propan-1-ol is 97.2 C. Explain, in terms of intermolecular forces, the difference between the boiling points of
these two compounds.
3 marks
Total 6 marks
END OF QUESTION AND ANSWER BOOK
2011 CHEM EXAM 1 2
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Question 1
Which one oI the Iollowing compounds is least soluble in water at room temperature?
A. ethane
B. ethanol
C. ethylamine
D. ethanoic acid
Question 2
The structure oI the product that is Iormed Irom the addition reaction between but-2-ene and chlorine, Cl
2
, is
A.

H C C C C
H H H H
Cl Cl H H
H
B.

H C C C C
H H H H
H Cl Cl H
H
C.

H C C C C
H Cl H H
H Cl H H
H
D.

Cl C C C C
H H H H
H H H H
Cl
SECTION A Multiple-choice questions
Instructions for Section A
Answer all questions in pencil on the answer sheet provided Ior multiple-choice questions.
Choose the response that is correct or that best answers the question.
A correct answer scores 1, an incorrect answer scores 0.
Marks will not be deducted Ior incorrect answers.
No marks will be given iI more than one answer is completed Ior any question.
3 2011 CHEM EXAM 1
SECTION A continued
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Question 3
Consider the Iollowing structures.
H
3
C C CH
2
CH CH
3
CH
3
CH
3
CH
3
H
3
C CH CH
2
C CH
3
CH
3
CH
3
CH
3
H
3
C CH CH
2
CH
2
C H
CH
3
CH
3
CH
3
I
II
III
IV
C CH
2
CH
2
CH CH
3
CH
3
CH
3
CH
3
H
Which oI the above structures is that oI 2,2,4-trimethylpentane?
A. I and III only
B. I and IV only
C. II and III only
D. II and IV only
Question 4
The compound that is not an isomer oI 2,2,4-trimethylpentane is
A. octane.
B. 3-ethylhexane.
C. 2,4-dimethylpentane.
D. 2,4-dimethylhexane.
2011 CHEM EXAM 1 4
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Question 5
The Iollowing is a diagram oI a section oI a protein chain.
Leu
Cys
Val
Val
Val Val
Asp
Asp
Asp
Asp
Val His
Tyr
Tyr
Leu
Leu
Tyr
Leu
Cys
Val
Cys
Tyr
Ser
His
Asp
Ala Ser
Cys
Cys
Cys
Asp
Tyr
Ala
Ser
Asp
Ala
Ala
Val
His
His
Cys
X
Y
Y
The bonds represented by X and Y are
X Y
A. amide bond disulfde bond
B. covalent bond ionic bond
C. hydrogen bond peptide bond
D. dipole-dipole bond covalent bond
Question 6
Alanine, lysine and aspartic acid are amino acids.
Which oI these will react with 1.0 M HCl(aq)?
A. lysine only
B. alanine and lysine only
C. aspartic acid and lysine only
D. alanine, aspartic acid and lysine
5 2011 CHEM EXAM 1
SECTION A continued
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Question 7
Halothane is a general anaesthetic. The Iollowing diagram represents the reaction pathway that produces halothane.
Cl
Cl
Cl Cl
H
C C
F
F H
F H C C
HF
SbCl
2
130 C
Cl F
F Br
F H C C
450 C
step 1 step 2 molecule X
Br
2
Which one oI the Iollowing correctly identifes the type oI reaction occurring in step 2 and correctly states the systematic
name oI molecule X?
Type of reaction in step 2 Systematic name of molecule X
A. substitution 1,2,2-trichloroethane
B. addition 1,1,2-trichloroethane
C. substitution 1,1,2-trichloroethene
D. addition 1,2,2-trichloroethene
2011 CHEM EXAM 1 6
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Question 8
The pain killer ibuproIen lysine is more soluble in water than ibuproIen and can thereIore be administered intravenously.
IbuproIen lysine is Iormed when ibuproIen and the amino acid, lysine, react with each other.
H
3
C
CH
3
CH
2
CH C O
CH
3
CH
H
C C N
H
H
O
OH
(CH
2
)
4
NH
2
+ ibuprofen lysine
ibuprofen lysine
OH
The structure oI the ibuproIen lysine is
H
H
3
N (CH
2
)
4
C
NH
2
+
D.
O

B.
A.
C.
CH
3
C N
O H
(CH
2
)
4
C
H
NH
2
OH
C
O
CH
3
CH
2
CH
CH
3
CH
H
C NH
2
(CH
2
)
4
NH
2
CH
3
C O
O
C
O
CH
3
CH
2
CH
CH
3
CH
CH
3
C
O
CH
3
CH
2
CH
CH
3
CH
OH
H
H
C
(CH
2
)
4
NH
2
CH
3
C N
O
CH
3
CH
2
CH
CH
3
CH
C
OH
O
C O
7 2011 CHEM EXAM 1
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Question 9
Canola oil is completely converted to biodiesel Iuel. One oI the components oI this biodiesel is ethyl stearate. Once
cooled, the product mixture oI the conversion oI canola oil to biodiesel separates into two layers. The top layer, layer
A, in the diagram, is the biodiesel Iuel.
layer A
layer B
The Iollowing chemicals are involved in the production oI biodiesel.
I glycerol
II potassium hydroxide
III ethanol
Which oI the above chemicals are Iound in layer B?
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
Question 10
Biogas can be generated as a by-product oI many Iarming activities. Waste waters oIten contain sugars, such as glucose,
which can be converted to methane. A simplifed reaction sequence is given below.
Step 1 Iermentation C
6
H
12
O
6
(aq) 2CH
3
CH
2
OH(aq) 2CO
2
(g)
Step 2 oxidation CH
3
CH
2
OH(aq) O
2
(aq) CH
3
COOH(aq) H
2
O(l)
Step 3 neutralisation 2CH
3
COOH(aq) CaCO
3
(s) Ca(CH
3
COO)
2
(aq) CO
2
(g) H
2
O(l)
Step 4 bacterial conversion Ca(CH
3
COO)
2
(aq) H
2
O(l) 2CH
4
(g) CO
2
(g) CaCO
3
(s)
The ratio oI the volume oI methane produced to volume oI carbon dioxide produced in the overall process is
A. 1:1
B. 1:2
C. 2:1
D. 2:3
2011 CHEM EXAM 1 8
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Question 11
Two titrations were perIormed as shown below.
0.20 M
NaOH
solution
25.0 mL of 0.10 M weak
monoprotic acid
25.0 mL of 0.10 M strong
monoprotic acid
Which one oI the Iollowing statements is true?
A. The weak acid will require a greater volume oI NaOH solution than the strong acid to reach the equivalence point.
B. The weak acid will require a smaller volume oI NaOH solution than the strong acid to reach the equivalence point.
C. The weak acid will require the same amount oI NaOH solution as the strong acid to reach the equivalence point.
D. The equivalence point in a titration oI a weak monoprotic acid with NaOH solution cannot be determined.
Question 12
To each oI three samples oI a solution, a diIIerent acid-base indicator is added. The Iollowing colours are observed.
Indicator Colour
thymol blue yellow
methyl red yellow
phenolphthalein colourless
The pH oI the solution is between
A. pH 2.8 and pH 4.2
B. pH 4.2 and pH 6.3
C. pH 6.3 and pH 8.3
D. pH 8.3 and pH 10.0
9 2011 CHEM EXAM 1
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Question 13
In an experiment, 172.1 g oI gypsum, CaSO
4
.2H
2
O, (M 172.1 g mol
1
), was heated to constant mass in a large crucible.
The loss in mass oI the crucible and contents was 27.0 g.
The reaction that occurred when the gypsum was heated was
A. CaSO
4
.2H
2
O(s) CaSO
4
(s) 2H
2
O(g)
B. 2CaSO
4
.2H
2
O(s) 2CaSO
4
.
1
2
H
2
O(s) 3H
2
O(g)
C. CaSO
4
.2H
2
O(s) CaSO
4
.H
2
O(s) H
2
O(g)
D. 2CaSO
4
.2H
2
O(s) 2CaSO
4
.
3
2
H
2
O(s) H
2
O(g)
Question 14
An analysis is carried out on a sample oI unknown gas. The density oI the gas is 2.86 grams per litre at STP.
The molecular Iormula oI the gas is
A. HCl
B. Cl
2
C. NO
2
D. SO
2
Question 15
Airbags are an important saIety Ieature oI today`s cars. The airbag contains a mixture oI solid sodium azide, NaN
3
, and
potassium nitrate, KNO
3
. In the event oI an accident, trip sensors send an electric signal to an igniter. The heat generated
causes the reactants to decompose completely according to the Iollowing equation.
10NaN
3
(s) 2KNO
3
(s) 5Na
2
O(s) K
2
O(s) 16N
2
(g)
A particular car`s airbag was Iound to infate to a volume oI 62.0 L at a pressure oI 100 kPa when the temperature
reached 36.6 C. The molar mass oI NaN
3
is 65.0 g mol
1
.
What was the mass oI sodium azide contained in the car`s airbag?
A. 97.9 g
B. 156.6 g
C. 250.6 g
D. 828.1 g
2011 CHEM EXAM 1 10
SECTION A continued
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Question 16
A starch molecule contains 500 glucose units.
II the molar mass oI glucose is 180 g mol
1
, then the molar mass oI the starch molecule is
A. 8 982 g mol
1
B. 81 018 g mol
1
C. 90 000 g mol
1
D. 98 982 g mol
1
Question 17
Two diIIerent Iood dye samples, W and Z, were compared using thin layer chromatography as shown below.
final solvent level
origin
samples W Z
A. Z is more strongly adsorbed than W and has a lower R
I
value.
B. Z is more strongly adsorbed than W and has a higher R
I
value.
C. W is more strongly adsorbed than Z and has a lower R
I
value.
D. W is more strongly adsorbed than Z and has a higher R
I
value.
Question 18
The IR wavenumber Ior bond stretching in a C-O bond (1000 1300 cm
1
) is lower than Ior a C-H bond (2850 3300 cm
1
).
Which one oI the Iollowing statements best explains this Iact?
A. Oxygen atoms are more electronegative than hydrogen atoms.
B. Oxygen atoms have a greater atomic mass than hydrogen atoms.
C. Oxygen atoms have a greater atomic radius than hydrogen atoms.
D. Oxygen atoms have a higher nuclear charge than hydrogen atoms.
11 2011 CHEM EXAM 1
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Question 19
Petrol is a mixture oI hydrocarbon molecules varying in size Irom six to ten carbon atoms. Forensic investigators suspect
that traces oI a substance Iound at a suspicious fre could be petrol that was used to start the fre.
Which one oI the Iollowing techniques could best be used to identiIy the substance?
A. NMR spectroscopy
B. UV-visible spectroscopy
C. atomic absorption spectroscopy
D. gas chromatography Iollowed by mass spectroscopy
Question 20
The amount oI copper in a solution oI copper (II) sulIate can be determined using atomic absorption spectroscopy.
When a blue copper (II) sulIate solution is introduced into an atomic absorption spectrometer, a green fame is observed.
Consider the Iollowing statements.
I A copper (II) sulIate solution appears blue because it absorbs red light.
II The metal species undergoes oxidation in the fame.
III The fame is green due to electron transitions Irom a higher energy state to a lower energy state.
Which oI the above statements are true?
A. I only
B. I and III only
C. II and III only
D. I, II and III
END OF SECTION A
TURN OVER
2011 CHEM EXAM 1 12
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SECTION B Question 1 continued
Question 1
Below are the structures oI a number oI important molecules.
A.

C
O
O
O
H
H
B.

O
CH
2
OH
H
OH
OH
OH
HO
H
H
H
H
C.

O
HOCH
2
OH
H
H
H
H H
OH
D.

C
13
H
27
C
O
O H
E.

H
C H OH
H OH
H OH
C
C
H
F.

C
17
H
31
C
O
O CH
3
G.

C
17
H
29
C
O
O H
H.
O
CH
2
OH
O O O
OH
OH
O
CH
2
OH
OH
OH
O
CH
2
OH
OH
OH O
H
H
H H H
H H H H
H
H
H
H
H
H
SECTION B Short answer questions
Instructions for Section B
Answer all questions in the spaces provided. Write using black or blue pen.
To obtain Iull marks Ior your responses you should
give simplifed answers with an appropriate number oI signifcant fgures to all numerical questions; unsimplifed
answers will not be given Iull marks.
show all working in your answers to numerical questions. No credit will be given Ior an incorrect answer unless
it is accompanied by details oI the working.
make sure chemical equations are balanced and that the Iormulas Ior individual substances include an indication
oI state; Ior example, H
2
(g); NaCl(s)
13 2011 CHEM EXAM 1
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SECTION B continued
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In each oI the Iollowing questions, circle the letter or letters that correspond to the compounds in the table on the
previous page.
The same letter may be used in more than one response.
a. Which molecule is used in the production oI acetylsalicylic acid?
A B C D E F G H
1 mark
b. Which molecule is the product oI a condensation polymerisation reaction?
A B C D E F G H
1 mark
c. Which two molecules are produced when a triglyceride containing no carbon-carbon double bonds undergoes
hydrolysis?
A B C D E F G H
2 marks
d. Which molecule could be a major component in biodiesel?
A B C D E F G H
1 mark
e. Which molecule is one oI the components that react to Iorm sucrose?
A B C D E F G H
1 mark
f. 0.001 mole oI which molecule will react completely with 0.320 g oI bromine?
A B C D E F G H
1 mark
Total 7 marks
2011 CHEM EXAM 1 14
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SECTION B Question 2 continued
Question 2
a. Bromine exists as two isotopes,
79
Br and
81
Br.
The mass spectrum oI bromoethane, C
2
H
5
Br, with two molecular ion peaks at m/z 108 and 110, is shown below.
100
80
60
40
20
0
relative
abundance
0 20 40 60 80 100 120
108
110
m/z
i. IdentiIy the species that produces the peak at m/z 29.
ii. What do the two molecular ion peaks indicate about the relative abundance oI
79
Br and
81
Br?
Give a reason Ior your answer.
1 2 3 marks
15 2011 CHEM EXAM 1
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SECTION B continued
TURN OVER
b. There are two compounds that have the molecular Iormula C
2
H
4
Br
2
.
The
1
H NMR spectrum oI one oI these compounds is provided below.
11 10 9 8 7 6 5 4 3 2 1 0
ppm
TMS
i. In the boxes below, draw the structural Iormula oI each oI the two compounds that have the molecular Iormula
C
2
H
4
Br
2
.
Structure 1 Structure 2
ii. Circle the structure above that corresponds to the
1
H NMR spectrum provided.
JustiIy your selection by reIerring to both the
1
H NMR spectrum and to the structure oI the compound.
2 3 5 marks
Total 8 marks
2011 CHEM EXAM 1 16
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SECTION B Question 3 continued
Question 3
CaIIeine is a stimulant drug that is Iound in coIIee, tea, energy drinks and some soIt drinks.
The concentration oI caIIeine in drinks can be determined using HPLC.
Four caIIeine standard solutions containing 50 ppm, 100 ppm, 150 ppm and 200 ppm were prepared. 25L oI each
sample was injected into the HPLC column. The peak areas were measured and used to construct the calibration graph
below. The chromatograms oI the standard solutions each produced a single peak at a retention time oI 96 seconds.
0
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
0 50 100 150 200
caffeine concentration (ppm)
peak area
(1000)
Peak area of caffeine standard solutions: retention time = 96 seconds
25L samples oI various drinks thought to contain caIIeine were then separately passed through the HPLC column.
The results are summarised below.
Sample Retention time of
major peak (seconds)
Peak area of largest
peak
SoIt drink A 96 12 000
SoIt drink B 32 8 500
Espresso coIIee 96 211 000
a. Determine the caIIeine content, in ppm, oI soIt drink A.
1 mark
17 2011 CHEM EXAM 1
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SECTION B Question 3 continued
TURN OVER
10 20 30 40 50 60 70 80 90 100 110 120
time (s)
standard (50 ppm)
20
15
10
5
10 20 30 40 50 60 70 80 90 100 110 120
time (s)
20
15
10
5
10 20 30 40 50 60 70 80 90 100 110 120
time (s)
20
15
10
5
10 20 30 40 50 60 70 80 90 100 110 120
time (s)
20
15
10
5
soft drink A
soft drink B
espresso
coffee
peak area
(1000)
peak area
(1000)
peak area
(1000)
peak area
(1000)
Chromatograms of 50 ppm standard caffeine solution,
soft drink A, soft drink B and espresso coffee
2011 CHEM EXAM 1 18
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SECTION B continued
b. What evidence is presented in the chromatogram that supports the conclusion that soIt drink B does not contain
any caIIeine?
1 mark
c. i. Explain why the caIIeine content oI the espresso coIIee sample cannot be reliably determined using the
inIormation provided.
ii. Describe what could be done to the espresso coIIee sample so that its caIIeine content can be reliably determined
using the inIormation provided.
1 1 2 marks
Total 4 marks
19 2011 CHEM EXAM 1
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SECTION B continued
TURN OVER
Question 4
Phosphorus is an essential ingredient in plant Iertiliser. The phosphorus content in Iertiliser can be determined as a
percentage, by mass, oI P
2
O
5
.
A 3.256 g sample oI Iertiliser is mixed with 40.0 mL oI deionised water and the insoluble residue is then removed using
vacuum fltration. 45.0 mL oI 10 MgSO
4
.7H
2
O solution is added to the fltrate Iollowed by 150.0 mL oI 2 M NH
3

solution. A white precipitate Iorms. This precipitate is fltered and washed with three 5 mL portions oI deionised water.
The fnal mass oI the precipitate, once thoroughly dried, was 4.141 g. The Iormula oI the precipitate is known to be
MgNH
4
PO
4
.6H
2
O. Assume that the experiment was conducted at 25 C and that all the phosphorus had been precipitated
as MgNH
4
PO
4
.6H
2
O.
a. Calculate the percentage, by mass, oI P
2
O
5
in the Iertiliser.
Molar mass oI MgNH
4
PO
4
.6H
2
O 245.3 g mol
1
. Molar mass oI P
2
O
5
142.0 g mol
1
.
4 marks
b. When MgNH
4
PO
4
.6H
2
O is heated above 100 C it is completely converted to MgNH
4
PO
4
according to the Iollowing
equation.
MgNH
4
PO
4
.6H
2
O(s) MgNH
4
PO
4
(s) 6H
2
O(g)
Would the calculated percentage by mass oI P
2
O
5
be higher, lower or the same as that determined in part a. iI the
precipitate collected had been deliberately heated above 100 C to completely convert the precipitate to MgNH
4
PO
4
beIore weighing? Explain your answer.
2 marks
Total 6 marks
2011 CHEM EXAM 1 20
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SECTION B Question 5 continued
Question 5
Glass made with the mineral tellurite, TeO
2
(M 159.6 g mol
1
), is oIten used to manuIacture optical fbres.
The amount oI tellurite in an ore sample can be determined by reaction with acidifed dichromate. In this reaction TeO
2

is converted to H
2
TeO
4
and Cr
2
O
7
2
is converted to Cr
3
.
a. The halI equation Ior the reduction oI the Cr
2
O
7
2
ion is
Cr
2
O
7
2
(aq) 14H

(aq) 6e

2Cr
3
(aq) 7H
2
O(l)
i. Write a balanced halI equation Ior the oxidation oI TeO
2
.
ii. Balance the chemical equation below by writing the coeIfcient oI each chemical species in the spaces provided.
TeO
2
(s) Cr
2
O
7
2
(aq) H

(aq) H
2
TeO
4
(aq) Cr
3
(aq) H
2
O(l)
1 1 2 marks
A 1.054 g ore sample containing tellurite is dissolved in acid. The resulting solution was then reacted with 50.00 mL oI
0.03052 M potassium dichromate, K
2
Cr
2
O
7
, solution to Iorm telluric acid, H
2
TeO
4
.
The amount oI unreacted dichromate ions, Cr
2
O
7
2
, in the above reaction, was then determined by titrating the solution
with 0.0525 M iron (II) nitrate, Fe(NO
3
)
2
, solution. An average titre volume oI 19.71 mL was required to reach the
equivalence point. The equation Ior this reaction is
6Fe
2
(aq) Cr
2
O
7
2
(aq) 14H

(aq) 2Cr
3
(aq) 6Fe
3
(aq) 7H
2
O(l)
b. i. Calculate the amount, in moles, oI excess dichromate ion.
21 2011 CHEM EXAM 1
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SECTION B continued
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ii. Calculate the amount, in moles, oI dichromate that reacted with the tellurite.
iii. Calculate the mass oI tellurite in the ore sample.
2 2 2 6 marks
Total 8 marks
2011 CHEM EXAM 1 22
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SECTION B continued
Question 6
a. i. The letters GATAC represent a part oI the base sequence in one strand oI DNA.
In the boxes provided write the base sequence oI the complementary strand oI DNA.
G A T A C
ii. Determine the number oI hydrogen bonds between the base pairings in this section oI DNA.
1 1 2 marks
Four diIIerent monomers known as nucleotides undergo condensation reactions to Iorm a strand oI DNA. The structure
oI one such nucleotide is shown below.
H
2
N
N
N
N
N
O
O
P
O

HO
OH
O
H H
H H
H
CH
2
b. Name the reactants that have combined in condensation reactions to Iorm this nucleotide.
3 marks
Total 5 marks

23 2011 CHEM EXAM 1
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SECTION B Question 7 continued
TURN OVER
Question 7
Banana oil, 3-methylbutylethanoate, CH
3
COOCH
2
CH
2
CH(CH
3
)
2
, is a sweet smelling liquid that gives bananas their
characteristic odour.
a. A chemist working Ior Go Bananas Pty Ltd has proposed the Iollowing reaction pathway Ior the synthesis oI banana
oil.
ClCH
2
CH
2
CH(CH
3
)
2
compound C
reaction I reagent A reaction II Cr
2
O
7
2
/H
+
compound B
CH
3
COOH
reaction III reagent D
CH
3
COOCH
2
CH
2
CH(CH
3
)
2
(banana oil, 3-methylbutylethanoate)
i. IdentiIy reagent A.
ii. Compound B is an alcohol.
Draw a structure oI compound B.
iii. Give the systematic name oI compound B.
iv. Give the systematic name oI compound C.
v. IdentiIy reagent D.
vi. Which reaction is an oxidation reaction? Circle the correct answer below.
reaction I reaction II reaction III
1 1 1 1 1 1 6 marks
2011 CHEM EXAM 1 24
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SECTION B continued
b. The chemist decided to use Iractional distillation to separate the fnal product Irom the reaction mixture. Describe
the principles oI Iraction distillation.
2 marks
The chemist compared the IR spectrum oI the banana oil aIter distillation with the IR spectrum oI a pure sample oI
compound B.
0.8
0.6
0.4
0.2
transmittance
3000 2000 1000
wavenumber (cm
1
)
infrared spectrum of compound B
wavenumber (cm
1
)
infrared spectrum of the banana oil
obtained after distillation
infrared spectrum infrared spectrum
0.8
0.6
0.4
0.2
transmittance
3000 2000 1000
The chemist claimed that these IR spectra indicate that a complete separation oI the banana oil Irom the reaction mixture
has been achieved.
c. Explain how the evidence provided by these spectra supports the chemist`s claim.
2 marks
Total 10 marks
25 2011 CHEM EXAM 1
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Question 8
Bradykinin is a peptide that lowers blood pressure.
Diagram I shows the amino acid sequence oI bradykinin.
ArgProProGlyPheSerProPheArg
diagram I
Diagram II shows the structure oI a section oI the bradykinin molecule.

N
H
C
H
C
O
N
H
C
H
C
O
OH CH
2
CH
2
diagram II
a. On diagram I, circle the section oI bradykinin that is represented in diagram II.
1 mark
b. Peptides can be completely hydrolysed to their component amino acids by treatment with 6 M HCl. IdentiIy the
two Iunctional groups that are Iormed as a result oI the hydrolysis oI the peptide link.
2 marks
c. Draw the chemical structure, showing all bonds, oI the amino acid glycine as it would exist in solution at
pH 1.
1 mark
Total 4 marks
END OF QUESTION AND ANSWER BOOK
2012 CHEM EXAM 1 2
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Question 1
H C
H
H
C
H
H
C
H
H
C
Cl
C
H
C
H
H
H
The correct systematic name for the compound shown above is
A. 2-chlorohex-2-ene
B. 3-chlorohex-2-ene
C. 3-chlorohex-3-ene
D. 4-chlorohex-5-ene
Question 2
The number of structural isomers of C
4
H
9
Cl is
A. 2
B. 3
C. 4
D. 5
SECTION A Multiple-choice questions
Instructions for Section A
Answer all questions in pencil on the answer sheet provided for multiple-choice questions.
Choose the response that is correct or that best answers the question.
A correct answer scores 1, an incorrect answer scores 0.
Marks will not be deducted for incorrect answers.
No marks will be given if more than one answer is completed for any question.
3 2012 CHEM EXAM 1
SECTION A continued
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Question 3
The following diagram is a simplied representation of a section of DNA.
X
Y
The main types of bonds at X and Y are
X Y
A.
ionic bonds hydrogen bonds
B.
covalent bonds dispersion forces
C.
dispersion forces ionic bonds
D.
covalent bonds hydrogen bonds
Question 4
In a double-stranded DNA sample, adenine constitutes 16% of the total number of bases.
The percentage of guanine content in the double strand is
A. 16%
B. 34%
C. 42%
D. 68%
2012 CHEM EXAM 1 4
SECTION A continued
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Question 5
Consider the following statements about the structure of proteins.
I The primary structure of a protein is determined by the sequence of amino acid residues.
II The secondary structure of a protein is the result of hydrogen bonding between NH and CO groups.
III The tertiary structure of a protein involves bonding between the side chains on the amino acid residues.
Of these statements
A. only I and III are true.
B. only I and II are true.
C. only II and III are true.
D. I, II and III are all true.
Question 6
Which one of the following amino acids is likely to be most polar in an aqueous solution at pH 7?
A. glutamic acid
B. glycine
C. leucine
D. valine
Question 7
Enzymes play an important role in biochemical reactions. Consider the following statements relating to
enzyme-catalysed reactions.
I The shapes of the substrate and the active site of the enzyme are complementary.
II When enzymes are denatured, the shape and structure of the active sites are not altered.
III The substrate forms bonds with the active site of the enzyme.
Of these statements
A. only I is true.
B. only III is true.
C. only I and III are true.
D. I, II and III are all true.
5 2012 CHEM EXAM 1
SECTION A continued
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Question 8
In the laboratory, salicylic acid can be used to produce two different compounds as shown in the diagram below.
These compounds are key components of pharmaceutical products.
H
H
H
HH
C C
C O H C
C
C
O
O H
C
H
3
C
O O
O
CH
3
reaction 1
reagent X
reaction 2
compound Y
H
H
H
HH
C C
C O CH
3
C
C
C
O
O H
C
H
2
O +
H
H
H
HH
C C
C O H C
C
C
O
O
O
C
C
CH
3
COOH
CH
3
+
C C
Which one of the following correctly identies reagent X and compound Y?
reagent X compound Y
A. methanol methyl salicylate
B. methanoic acid methyl salicylate
C. methanoic acid acetylsalicylic acid (aspirin)
D. methanol acetylsalicylic acid (aspirin)
2012 CHEM EXAM 1 6
SECTION A continued
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Use the following information to answer Questions 911.
H C
H
H
H
H
H
H
H
H
C C
O
O C C H
Question 9
Which one of the following is the correct systematic name of this compound?
A. ethyl propanoate
B. ethyl ethanoate
C. propyl ethanoate
D. propyl pentanoate
Question 10
The species that produces the molecular ion peak in the mass spectrum of this compound is
A. [CH
3
CH
2
COOCH
2
CH
3
]
+
B. [CH
3
CH
2
COOCH
2
CH
3
]
2+
C. [CH
3
CH
2
COOCH
2
CH
3
]

D. CH
3
CH
2
COOCH
2
CH
3
7 2012 CHEM EXAM 1
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SECTION A continued
TURN OVER
Question 11
Which one of the following infrared (IR) spectra is consistent with the structure of this compound?
Due to copyright restriction,
this material is not supplied.
Source: Spectral Database for Organic Compounds SDBS
2012 CHEM EXAM 1 8
SECTION A continued
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Question 12
The following chromatogram was produced when 0.1 g of decane was passed through a gas chromatography
column.
20000
10000
detector
response
5 10 15 20
retention time (min)
The chromatogram produced when 0.2 g of decane is passed through the same column under identical conditions is
best represented by
A.

20 000
10 000
5 10
retention time (min)
15 20
detector
response
B.

20 000
10 000
5 10
retention time (min)
15 20
detector
response
C.

20 000
10 000
5 10
retention time (min)
15 20
detector
response
D.

20 000
10 000
5 10
retention time (min)
15 20
detector
response
Question 13
15.0 mL of 10.0 M HCl is added to 60.0 mL of deionised water.
The concentration of the diluted acid is
A. 3.33 M
B. 2.50 M
C. 2.00 M
D. 0.500 M
9 2012 CHEM EXAM 1
SECTION A continued
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Question 14
A desalination plant produces 200 gigalitres (GL) of fresh water each year. The maximum level of boron permitted in
desalinated water is 0.5 ppm (0.5 mg L
1
). The maximum mass, in kilograms, of boron that is permitted in one years
production of desalinated water is
A. 9.26 10
3
B. 1.0 10
5
C. 1.08 10
6
D. 1.0 10
8
Question 15
A sample of the anticancer drug Taxol

, C
47
H
51
NO
14
, contains 0.157 g of carbon.
The mass, in grams, of oxygen in the sample is
A. 0.0468
B. 0.0624
C. 0.209
D. 0.703
Question 16
A helium balloon is inated to a volume of 5.65 L and a pressure of 10.2 atm at a temperature of 25 C.
The amount of helium, in moles, in the balloon is
A. 0.023
B. 0.276
C. 2.36
D. 27.95
2012 CHEM EXAM 1 10
SECTION A continued
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Question 17
Which titration curve best represents the change in pH as 0.100 M NaOH solution is added to a 10.0 mL aliquot of
0.100 M HCl solution?
A.

14
12
10
8
6
4
2
0
0 0.005 0.010 0.015 0.020
pH
volume, in litres, of NaOH added
B.

14
12
10
8
6
4
2
0
0 0.005 0.010 0.015 0.020
pH
volume, in litres, of NaOH added
C.

14
12
10
8
6
4
2
0
0 0.005 0.010 0.015 0.020
pH
volume, in litres, of NaOH added
D.

14
12
10
8
6
4
2
0
0 0.005 0.010 0.015 0.020
pH
volume, in litres, of NaOH added
Question 18
2.1 g of an alkene that contains only one double bond per molecule reacted completely with 8.0 g of bromine, Br
2
.
The molar mass of bromine, Br
2
, is 160 g mol
1
.
Which one of the following is the molecular formula of the alkene?
A. C
5
H
10
B. C
4
H
8
C. C
3
H
6
D. C
2
H
4
Question 19
The oxidation state of phosphorus in the pyrophosphate ion P
2
O
7
4
is
A. +3.5
B. +5
C. +7
D. +10
11 2012 CHEM EXAM 1
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Question 20
Consider the following reaction.
IO
3

(aq) + 5I

(aq) + 6H
+
(aq) 3I
2
(s) + 3H
2
O(l)
The correct half equation for the reduction reaction is
A. 2I

(aq) I
2
(s) + 2e

B. 2H
+
(aq) + 2e

H
2
O(l)
C. IO
3

(aq) + I

(aq) I
2
(s) + 3O
2
(aq) + 4e

D. 2IO
3

(aq) + 12H
+
(aq) + 10e

I
2
(s) + 6H
2
O(l)
END OF SECTION A
TURN OVER
2012 CHEM EXAM 1 12
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SECTION B Question 1 continued
Question 1
a. The cellulose that is present in plant matter cannot be directly fermented to produce bioethanol. The cellulose
polymer must rst be broken down into its constituent monomers.
A section of cellulose polymer is shown below.
H
H
H
H H
OH
OH H
CH
2
OH
CH
2
OH
O
O
O
OH
OH
H
H
H
H
O
O
H
H
H
H H
OH
OH H
CH
2
OH
CH
2
OH
O
O
OH
OH
H
H
H
H
O
O
i. What is the name of the monomer from which cellulose is formed?
ii. Complete the following chemical equation to show the formation of ethanol by fermentation of the
cellulose monomer.
C
6
H
12
O
6
(aq) +
iii. Ethanol can be manufactured directly from ethene gas in the presence of a catalyst. Write a balanced
equation for this reaction.
1 + 1 + 1 = 3 marks
SECTION B Short answer questions
Instructions for Section B
Answer all questions in the spaces provided. Write using black or blue pen.
To obtain full marks for your responses you should
give simplied answers with an appropriate number of signicant gures to all numerical questions;
unsimplied answers will not be given full marks.
show all working in your answers to numerical questions. No credit will be given for an incorrect answer
unless it is accompanied by details of the working.
make sure chemical equations are balanced and that the formulas for individual substances include an
indication of state; for example, H
2
(g); NaCl(s).
13 2012 CHEM EXAM 1
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SECTION B continued
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b. Triglycerides are an important source of energy in the body. During digestion, triglycerides are broken down
in the small intestine by the enzyme lipase. An incomplete chemical equation that shows the hydrolysis of a
triglyceride is shown below.
H
C
C
C
O
O
O
H
H
H
H
O
C
C
C
O
C
(CH
2
)
16
CH
3
(CH
2
)
16
CH
3
+ 3H
2
O
(CH
2
)
16
CH
3
CH
3
(CH
2
)
16
COOH
product A product B
+
C
3
H
8
O
3
i. In the spaces provided above, balance the equation by adding appropriate coefcients for product A and
product B.
ii. Name the fatty acid that is produced by the hydrolysis of this triglyceride.
iii. The fatty acid produced in the above reaction is completely oxidised to produce carbon dioxide and water.
Write a balanced equation for the oxidation reaction.
1 + 1 + 2 = 4 marks
2012 CHEM EXAM 1 14
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SECTION B Question 2 continued
Question 2
A drop that contains a mixture of four amino acids was applied to a thin layer chromatography plate. The plate was
placed in solvent G and the following chromatogram was obtained.
spot 1
solvent front: solvent G
B C
A D
application
point of drop
chromatogram I
The R
f
values for each of the amino acids in solvent G are provided in Table 1 below.
Table 1. R
f
values in solvent G
amino acid R
f
(solvent G)
alanine 0.51
arginine 0.16
threonine 0.51
tyrosine 0.68
a. Name the amino acid that corresponds to spot 1.
1 mark
15 2012 CHEM EXAM 1
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SECTION B continued
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The plate was dried, rotated through 90 in an anticlockwise direction and then placed in solvent F. The R
f
values for
each of the amino acids in solvent F are provided in Table 2 below.
Table 2. R
f
values in solvent F
amino acid R
f
(solvent F)
alanine 0.21
arginine 0.21
threonine 0.34
tyrosine 0.43
The following chromatogram was obtained.
C D
B A
chromatogram II
solvent front: solvent F
solvent front:
solvent G
application
point of drop
b. Circle the spot on chromatogram II that represents alanine.
1 mark
c. Explain, in terms of the data provided, why only three spots are present in chromatogram I while four spots are
present in chromatogram II.
2 marks
2012 CHEM EXAM 1 16
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SECTION B Question 3 continued
Question 3
Sections of the primary structure of nylon and the primary structure of a protein are shown below.
C
O
(CH
2
)
4
C
O
C
O
N
H
(CH
2
)
6
(CH
2
)
4
(CH
2
)
4
(CH
2
)
6
C
O
N C
O
C
O
H
N
H
N
H
nylon
O
N
H
C N
O O O O
C N CH
2
C CH
2
C N C N CH(CH
3
) CH(CH
3
) CH
2
H H H H
protein
Nylon is composed of two monomers. The structure of one of the monomers is provided below.
O
H H O O
C
O
C (CH
2
)
4
a. Draw the structure of the other monomer.
1 mark
b. Name the functional groups that link the monomers in
nylon.
protein.
2 marks
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SECTION B continued
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c. Look carefully at the functional group that links monomers in protein and nylon. The functional groups that
connect the protein monomers are oriented in the same direction. The functional groups that link the nylon
monomers are oriented in opposing directions.
Explain why the functional groups that link the monomers in protein are oriented differently from the functional
groups that link the monomers in nylon. Make appropriate reference to the structures of nylon and protein
monomers in your answer.
2 marks
d. Perspex (polymethyl methacrylate) is a clear, colourless polymer used for optical applications. The structural
formula of the only monomer used in the synthesis of perspex, methyl methacrylate, is shown below.
H
2
C
C
C
CH
3
CH
3
O
O
Draw a section of the polymer showing at least two units of the monomer.
2 marks
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SECTION B continued
Question 4
a. Give the systematic names of the alkanol and the carboxylic acid that are required to synthesise propyl
propanoate.
2 marks
b. Write a balanced chemical equation for the synthesis of propyl propanoate. Use the semi-structural formula for
the reactants and products.
2 marks
c. Describe the steps that are required to prepare a sample of pure propyl propanoate using only a pure sample of
the alkanol as the starting reagent. Include any reagents that are used in the synthesis. An annotated ow chart
may be used in your answer.
3 marks
d. Identify one method that could be used to verify that the substance produced is pure propyl propanoate. Explain
how this method would indicate that the product is pure propyl propanoate.
2 marks
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SECTION B Question 5 continued
Question 5
An organic chemist found a bottle in the laboratory that was labelled organic cleaning uid, C
3
H
8
O. She decided to
test the liquid. The chemist obtained the following data about the compound in the cleaning uid: the
1
H NMR and
13
C NMR spectra, and the infrared spectrum.
The
1
H NMR data is summarised in the table below.
Chemical shift (ppm) Relative peak area Peak splitting
1.2 6 doublet (2)
2.2 1 singlet (1)
3.6 1 septet (7)
6 5.5 5 4.5 4 3.5 3 2.5 2 1.5 1 0.5 0
TMS
signal
TMS
signal
chemical shift (ppm)
1
H NMR spectrum
chemical shift (ppm)
70 60 50 40 30 20 10 0
13
C NMR spectrum
a. i. How many different carbon environments are present in the compound?
ii. How many different hydrogen environments are present in the compound?
iii. In the
1
H NMR spectrum, the signal at 3.6 ppm is split into a septet (7 peaks). What is the number of
equivalent protons that are bonded to the adjacent carbon atom(s)?
1 + 1 + 1 = 3 marks
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Infrared spectrum
3500 3000 2500 2000 1500 1000 500
absorption
wavenumber (cm
1
)
A
b. Using the Infrared absorption data on page 7 of the Data Book, identify the atoms that are associated with the
absorption labelled A on the infrared spectrum.
1 mark
c. Draw a structure of the compound in the cleaning uid that is consistent with the NMR and IR data.
1 mark
2012 CHEM EXAM 1 22
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SECTION B Question 6 continued
Question 6
The iron content in multivitamin tablets was determined using atomic absorption spectroscopy.
The absorbances of four standards were measured.
Three multivitamin tablets were selected. Each tablet was dissolved in 100.0 mL of water. The absorbance of each of
the three solutions was then measured.
The following absorbances were obtained.
Solution
Concentration
mg/L
Absorbance
Standard 1 0.00 0.06
Standard 2 100.0 0.16
Standard 3 200.0 0.25
Standard 4 300.0 0.36
Standard 5 400.0 0.46
Tablet 1 0.39
Tablet 2 0.42
Tablet 3 0.45
a. i. Use the grid below to construct a calibration graph of the absorbances of the standard solutions.
0.8
0.6
0.4
0.2
100 200
concentration (mg/L)
300 400
absorbance
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ii. Determine the average iron content, in milligrams, of the multivitamin tablets.
2 + 2 = 4 marks
Spectroscopic techniques work on the principle that, under certain conditions, atoms, molecules or ions will interact
with electromagnetic radiation. The type of interaction depends on the wavelength of the electromagnetic radiation.
b. Name one spectroscopic technique that you have studied this year.
i. Which part of the electromagnetic spectrum does this technique use?
ii. How does this part of the electromagnetic spectrum interact with matter? What information does this
spectroscopic technique provide?
1 + 2 = 3 marks
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SECTION B Question 7 continued
Question 7
Students in a chemistry class were required to design a procedure to determine gravimetrically the concentration of
lead(II) ethanoate, Pb(CH
3
COO)
2
, in a sample of hair dye. They were instructed to measure the mass of precipitate
formed when a sample of the hair dye was added to either 0.1 M potassium iodide or 0.1 M potassium nitrate.
The students were also provided with the following data.
Name Formula Relative molar mass Solubility at 25 C (g/100 g)
lead(II) ethanoate Pb(CH
3
COO)
2
325.3 55.0
lead(II) iodide PbI
2
461.0 0.076
lead(II) nitrate Pb(NO
3
)
2
331.2 60.0
Student A decided to precipitate the lead(II) ions in the hair dye as lead(II) iodide. She added an excess of 0.1 M KI
solution to 20.0 mL of hair dye. The yellow precipitate was ltered using pre-weighed lter paper. The precipitate
was then washed with distilled water. The precipitate and lter paper were gently heated, allowed to cool and then
weighed. This step was repeated several times.
Student As results are summarised below.
Volume of hair dye solution 20.0 mL
Mass of lter paper 0.3120 g
Mass of lter paper plus precipitate after rst heating 0.4831 g
Mass of lter paper plus precipitate after second heating 0.4059 g
Mass of lter paper plus precipitate after third heating 0.4059 g
Mass of lter paper plus precipitate after fourth heating 0.4059 g
a. i. Write a balanced equation for the precipitation of lead(II) iodide.
ii. Explain why the lter paper and precipitate were heated and weighed several times.
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iii. Calculate the mass, in grams, of lead(II) iodide formed.
iv. What is the mass, in grams, of lead(II) ethanoate that is present in 100.0 mL of hair dye solution?
1 + 1 + 1 + 3 = 6 marks
Student B decided to precipitate the lead(II) ions in the hair dye as lead(II) nitrate. However, he did not produce any
precipitate.
b. Explain why no precipitate of lead(II) nitrate formed.
1 mark
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SECTION B Question 8 continued
Question 8
The solubility of highly soluble, thermally unstable salts such as ammonium chloride may be determined by back
titration.
In one experiment a 5.00 mL saturated solution of ammonium chloride, NH
4
Cl, at 20.0 C, was diluted with distilled
water to 250.0 mL in a standard ask.
A 20.0 mL aliquot of this solution was added to 10.0 mL of 0.400 M NaOH solution. The solution was heated to
drive off the ammonia formed by this reaction.
When the ask had cooled, the excess hydroxide ions were neutralised by 14.7 mL of 0.125 M HCl solution. The
molar mass of ammonium chloride is 53.5 g mol
1
.
a. i. Write an equation for the neutralisation reaction.
ii. Determine the amount, in mole, of NaOH that was originally added to the ammonium chloride solution.
iii. Determine the amount, in mole, of ammonium chloride in the 20.0 mL aliquot.
iv. Calculate the amount, in mole, of ammonium chloride in 5.00 mL of the saturated solution.
v. Calculate the solubility, in gL
1
, of ammonium chloride in water at 20 C.
1 + 1 + 2 + 1 + 2 = 7 marks
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b. If the burette was rinsed with water instead of acid before the titration, how would the calculated solubility of
ammonium chloride be affected? Explain your answer.
2 marks
END OF QUESTION AND ANSWER BOOK