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CCC Olympiad 2016-2019

The document outlines the Canadian Chemistry Contest 2019, specifically Part A, which consists of multiple-choice questions covering various chemistry topics. Contestants are required to use only the provided periodic table and a scientific calculator, with specific instructions on answer submission. The questions range from solution concentrations to thermodynamics and chemical reactions, testing participants' knowledge and application of chemistry principles.

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0% found this document useful (0 votes)

74 views91 pages

CCC Olympiad 2016-2019

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THE CANADIAN CHEMISTRY CONTEST 2019

PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)

All contestants should attempt this part of the contest before proceeding to Part B and/or Part C.
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

1) A solution is 0.0240 mol L-1 KI and 0.0146 mol L-1 MgI2. What volume of 5) The melting point of CaS is higher than that of KCl. Explanations for this
water should be added to 100.0 mL of this solution to produce a observation include which of the following?
solution with [I-] concentration of 0.0500 mol L-1?
I. Ca2+ is more positively charged than K+.
II. S2– is more negatively charged than Cl–.
A) 106.4 mL B) 53.2 mL C) 26.6 mL D) 13.3 mL E) 6.4 mL
. III. The K+ ion is smaller than the Ca2+ ion.
2) The boiling points of the compounds acetic acid (CH3COOH), 1-pentanol
(C5H11OH), dibutyl ether (C8H18O) and dodecane (C12H26) increase in A) II only B) I and II only C) I and III only
that order. Which of the following statements provides the best D) II and III only E) I, II, and III
explanation for this increase?
6) Fluorine is the most electronegative element on the periodic table. As a
result it always forms polar bonds with other non-metals. Despite this,
A) The London dispersion forces increase which of the following fluorine containing compounds would be a non-
B) The hydrogen bonding increases polar molecule?
C) The dipole-dipole forces increase
D) The chemical reactivity increases A) SF4 B) PF3 C) IF5 D) BrF3 E) XeF4
E) The number of carbon atoms increases
7) Ronald James Gillespie, who developed Valence Shell Electron Pair
3) Health Canada recommends that women between the ages of 12 and 45 Repulsion (VSEPR) theory, isolated the superacid fluorosulfuric acid
consume 400 micrograms of folic acid (C19H19N7O6) per day, which (HSO3F) when he combined fluorinated compounds with concentrated
reduces the risk of neural tube defects during pregnancy. How many sulfuric acid, creating brightly coloured solutions. Which of the
moles of folic acid are equivalent to 400 micrograms?
following best describes the molecular shape of fluorosulfuric acid, as
predicted by VSEPR theory?
A) 1.10 mmol B) 0.177 mol C) 0.906 mol
D) 0.906 mmol E) 9.06 x 10-7 mol
A) See saw B) Trigonal bipyramidal C) Tetrahedral
4) An unknown amino acid contains 9.5 % nitrogen by mass as determined D) Square planar E) Trigonal pyramidal
by elemental analysis. Which of the following could be the unknown
amino acid?
8) Vinegar used as a cooking ingredient, or in pickling, is a solution of 5%
acetic acid (CH3COOH) by mass in solution with water. The pKa= 4.76
A) arginine C6H14N4O2 B) cysteine C3H7NO2S
for acetic acid at 25°C. Evaluate the pH of vinegar at 25 °C.
C) histidine C6H9N3O2 D) glutamic acid C5H9NO4
E) glycine C2H5NO2
A) 4.80 B) 4.15 C) 2.92 D) 2.42 E) 2.24
CCC 2019 page 2 of 4

9) The ionization energies for period 3 element X are listed in the table 11) Given the following electrochemical cell data:
below. Cell 1 Cd(s) | Cd2+ (1.0M) || Cu2+ (1.0M) | Cu(s) Eo = +0.74 V
Cell 2 Zn(s) | Zn2+ (1.0 M) || Cu2+ (1.0 M) | Cu(s) Eo = +1.10 V
Cell 3 Zn(s) | Zn2+ (1.0 M) || Cd2+ (1.0 M) | Cd(s)
Ionization Energies for element X (kJ mol-1)
First Second Third Fourth Fifth Determine the standard cell potential for Cell 3.
580 1,815 2,740 11,600 14,800
A) – 0.36 V B) 0.36 V C) –1.84 V
D) –0.18 V E) 0.18 V
Based on the data, which statement about element X is FALSE?
12) Lead (II) sulfate can decompose into lead (II) sulfite and oxygen gas
A) Its most common oxidation state is +3 when heated. If the reaction generates 2.25 g of oxygen gas, what mass
B) It is displaced from aqueous solution by copper metal of lead (II) sulfate reacted? Assume 100% yield in this reaction.
C) It is the most abundant metal in the Earth’s crust
D) Its oxide is insoluble in water A) 42.6 g B) 21.3 g C) 20.2 g D) 10.7 g E) 4.50 g
E) It is a lustrous metal
13) A student combines 75 mL of 0.500 mol L-1 hydrochloric acid with
10) Stavzor (structure below) is a medication primarily used to treat epilepsy and 55 mL of 0.125 M KOH. What is the pH of the resulting solution?
bipolar disorder.
A) 0.30 B) 0.39 C) 0.63 D) 1.51 E) 7.00
HO O
14) A system undergoes a reversible cyclic process and proceeds through
Stavzor a series of thermodynamic processes, exchanging heat and work with
its surroundings and ultimately returning to its original state. Which
one of the following statements is true? Assume that the surroundings
A well-known substance with a characteristic odour of bananas (A) is a are much larger than the system.
constitutional isomer of Stavzor. Which of the following is a possible
structure for A? A) ∆Ssurroundings > 0 B) q > 0 C) q < 0 D) q = w = 0 E) ∆S > 0

O 15) The thermite reaction is the reaction of aluminum metal and iron (III)
O OH O O
oxide:
(a) (b) (c) O 2 Al (s) + Fe2O3 (s) → Al2O3 (s) + 2 Fe (s) ∆H = –852 kJ

A teacher does a demonstration with 1.00 mol of iron (III) oxide and
O O O 2.00 mol of aluminum metal both initially at 25.0 °C. If the combined
(d) (e) specific heat of the products is 0.800 J g-1 °C-1 over a wide range of
O temperatures, what is the final temperature of the products?

A) 3550°C B) 4960 °C C) 5010 °C D) 6470 °C E) 6500°C

CCC 2019 page 3 of 4

16) The compound acetanilide is important in the industrial synthesis of 18) Given the following set of equilibria and their respective constants
several dyes. Acetanilide (mol. wt. = 135.16) can be made in the
laboratory by a reaction between aniline and excess acetic anhydride NH4+ ⇌ H+ + NH3 Ka = 5.6 x 10–10
which has a yield of 61.5%: H2CO3 ⇌ H+ + HCO3– Ka1 = 4.2 x 10–7
HCO3–⇌ H+ + CO32– Ka2 = 2.4 x 10–8
NH2
O what would the equilibrium constant be for the reaction below?
O O
+ H2CO3 + 2 NH3 ⇌ (NH4)2CO3 K=?
N
O
H A) 1.8 x 10–5 B) 4.4 x 10–7 C) 9.0 x 10–6
aniline acetic anhydride acetanilide D) 3.2 x 104 E) 3.1 x 10–5

Aniline and acetic anhydride are both liquids which have densities of
1.219 g mL-1 and 1.082 g mL-1 respectively.
19) The subshell filling order used for the quantum mechanical model of
What volume of aniline was used in this reaction if the recorded mass of the atom is an approximation of the relative subshell energies, which
acetanilide product was 7.14 g? assumes the energies remain fixed. However, there are exceptions to
the Aufbau Principle. Which of the following is the correct ground state
A) 4.03 mL B) 9.75 mL C) 4.92 mL configuration of an element found on the periodic table?
D) 5.99 mL E) 6.56 mL
A) [Ar] 4s1 3d5 B) [Ar] 4s2 3d4 C) [Ar] 4s2 4d4
17) One of the Twelve Principles of Green Chemistry is that “synthetic
methods should be designed to maximize the incorporation of all D) [Ar] 4s2 4p4 E) [Ar] 4s1 4p5
materials used in the process into the final product”. One way to
consider this is to calculate the atom economy (AE) of a chemical
reaction where AE is defined as follows:
20) A vessel contains 2.50 mol of O2 gas, 0.50 mol of N2 gas and 1.00 mol of
𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑜𝑜𝑜𝑜 𝑑𝑑𝑑𝑑𝑑𝑑𝑑𝑑𝑑𝑑𝑑𝑑𝑑𝑑 𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝𝑝 CO2 gas. The total pressure is 200 kPa. The partial pressure exerted by
𝑎𝑎𝑎𝑎𝑎𝑎𝑎𝑎 𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒𝑒 = × 100%
𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑚𝑚𝑚𝑚𝑚𝑚𝑚𝑚 𝑜𝑜𝑜𝑜 𝑎𝑎𝑎𝑎𝑎𝑎 𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟𝑟 the O2 in the mixture is:

A) 25 kPa B) 50 kPa C) 100 kPa D) 125 kPa E) 150 kPa

The atom economy of the reaction in the previous question (#16) is:

A) 61.5% B) 69.2% C) 100% D) 68.9% E) 74.4%

CCC 2019 page 4 of 4

21) The O2 (g) produced in the decomposition of 3.275 g mixture of 23) For the reaction H2 (g) + I2 (g) ⇌ 2 HI (g) ∆H° = +52.96 kJ.
potassium chlorate and potassium chloride which is 65.82% KClO3 by Which of the following statement(s) is/are correct?
mass is collected over water at 21.0 °C. Assume ideal gas conditions. If
atmospheric pressure is 753.5 mmHg, water vapour pressure at 21.0°C I. The heat of formation of 1 mol of HI is +26.48 kJ
is 18.7 mmHg, once the pressure in the gas collection vessel was II. As the temperature increases, the reaction will proceed to the
equalized with atmospheric pressure, how many milliliters of O2 gas right
would be produced according to the reaction: III. As the pressure increases, the reaction will proceed to the
right
2 KClO3 (s) → 2 KCl (s) + 3 O2 (g)
A) I only B) I and II only C) I, II and III
D) II and III only E) III only

24) Calculate ∆G° at 25 °C for the reaction given the data below
KClO3
4 HCl (g) + O2 (g) → 2 Cl2 (g) + 2 H2O (g) ∆H° = –114.4 kJ
O2 𝑜𝑜
𝑆𝑆𝐶𝐶𝐶𝐶 2
= 223.0 J mol-1 K-1 𝑆𝑆𝐻𝐻𝑜𝑜2𝑂𝑂 = 188.7 J mol-1 K-1,
𝑜𝑜
𝑆𝑆𝑂𝑂𝑜𝑜2 = 205.0 J mol-1 K-1 𝑆𝑆𝐻𝐻𝐻𝐻𝐻𝐻 = 186.8 J mol-1 K-1

A) + 14.4 kJ B) –111.18 kJ C) + 3105.6 kJ

D) + 38 kJ E)– 76.0 kJ

A) 130 mL B) 439 mL C) 563 mL 25) For the reaction 2 NO (g) + Cl2 (g) → 2 NOCl (g) the table below
D) 658 mL E) 1320 mL provides experimental data for 3 different reactions.

22) The equilibrium CO (g) + NO2 (g) ⇌ CO2(g) + NO (g) is established in Experiment [NO] (mol L-1) [Cl2] (mol L-1) Initial Rate
four different, but identical containers. Each container started with a (mol L-1s-1)
different composition as follows: 1 0.0125 0.0128 1.14 x 10-5
2 0.0125 0.0511 4.55 x 10-5
Container CO (mol) NO2 (mol) CO2 (mol) NO (mol) 3 0.0250 0.0255 9.08 x 10-5
1 1 1 0 0
2 1 0 1 1 What is the rate constant for the reaction?
3 1 1 1 0
4 0 1 1 1 A) 140 L mol-1 s-1 B) 0.0714 L mol-1 s-1 C) 5.70 L2 mol-2 s-1
5 1 1 1 1 D) 0.562 L mol-1 s-1 E) 1.39 L2 mol-2 s-1

After equilibrium is established, which container would have the largest

End of Part A of the contest
concentration of CO (g)
Go back and check your work
A) 1 B) 2 C) 3 D) 4 E) 5
THE 2019 CANADIAN CHEMISTRY CONTEST
for High School and CEGEP Students
PART B – EXTENDED RESPONSE SECTION (90 minutes)

Students will answer TWO questions as follows: all students must answer the experimental design
question 1; students have the choice between answering either question 2 or question 3. For each
question, students should write a scientific essay including appropriate equations, formulae and diagrams.
Each essay is of equal value. Allocate approximately equal time to each question. Scorers will consider the
accuracy and quality of the information and the presentation of the responses. A clear, concise, well-
organized piece of written work will be rated more highly than a long rambling one. A scientific calculator
is allowed. No phones or communication devices are allowed.

1) Experimental Design: Heat of Combustion of Paraffin (mandatory question)

Design an experiment to measure the heat of combustion of paraffin wax in a candle. You may use any
equipment, reagents, and materials typically found in a high school chemistry classroom. In addition, you
have an empty soft drink can with two holes, 0.5 cm in diameter, on the top. You also have a large empty
metal can open at both ends, which you could put around the candle to reduce drafts. On the counter, you
have water, a ring clamp, retort stand, ice cubes, a balance, thermometer, graduated cylinders, glass stirring
rod and tongs. Clearly present your experimental steps and the reasoning behind them. You must
demonstrate a thorough understanding of the experiment you are performing, the data you need to collect,
and the data analysis you must perform.
2) The Chemistry Contributions of Gilbert Lewis

One of the most recognizable names for high school chemistry students is that of Gilbert Lewis. Young
chemistry students start understanding atoms and compounds by drawing Lewis Dot Diagrams. Senior
Chemistry students expand their understanding of chemistry by studying Lewis acids and bases. Discuss
your understanding of the significance of Lewis’ contributions to Chemistry. In your discussion, you should
explain Lewis’ influence on better understanding chemical structures, bonding, electron transfer and acid
base chemistry.

3) 2019: The International Year of the Periodic Table

The United Nations, Educational, Scientific and Cultural Organization’s (UNESCO) declared 2019 the
International Year of the Periodic Table in celebration of the 150th anniversary of Dimitry Mendeleev’s
1869 creation. UNESCO states: “The Periodic Table of Chemical Elements is one of the most significant
achievements in science, capturing the essence not only of chemistry, but also of physics and biology”.
Discuss the statement UNESCO made about the periodic table and explain why UNESCO claims that the
periodic table is one of the most significant achievements in science. Use several concrete examples of the
periodic table’s importance in chemistry and at least 1 example of the importance of the periodic table in
Physics and in Biology.
THE CANADIAN CHEMISTRY CONTEST 2019
for high school and CEGEP students
(formerly the National High School Chemistry Examination)

PART C: CANADIAN CHEMISTRY OLYMPIAD

Final Selection Examination 2019
Free Response Development Problems (90 minutes)
This segment has five (5) questions. While students are expected to attempt all questions for a
complete examination in 1.5 hours, it is recognized that backgrounds will vary and students will
not be eliminated from further competition because they have missed parts of the paper.

Your answers are to be written in the spaces provided on this paper. All of the paper, including
this cover page, along with a photocopy of Part A of the examination, is to be returned
IMMEDIATELY by courier to your Canadian Chemistry Olympiad Coordinator.

— PLEASE READ — PART A ( )

Correct Answers
1. BE SURE TO COMPLETE THE INFORMATION REQUESTED AT THE
BOTTOM OF THIS PAGE BEFORE BEGINNING PART C OF THE
EXAMINATION. 25 x 1.6 = ......... /040

2. STUDENTS ARE EXPECTED TO ATTEMPT ALL QUESTIONS OF

PART C
PART A AND PART C. CREDITABLE WORK ON A LIMITED
NUMBER OF THE QUESTIONS MAY BE SUFFICIENT TO EARN AN 1. .................... /012
INVITATION TO THE NEXT LEVEL OF THE SELECTION PROCESS.
2. .................... /012
3. IN QUESTIONS WHICH REQUIRE NUMERICAL CALCULATIONS, BE
SURE TO SHOW YOUR REASONING AND YOUR WORK.
3. .................... /012

4. .................... /012
4. ONLY NON-PROGRAMMABLE CALCULATORS MAY BE USED ON
THIS EXAMINATION. 5. .................... /012

5. NOTE THAT A PERIODIC TABLE AND A LIST OF SOME PHYSICAL

CONSTANTS WHICH MAY BE USEFUL CAN BE FOUND ON A DATA
SHEET PROVIDED AT THE END OF THIS EXAMINATION.
TOTAL ............. /100
Name _____________________________ School ____________________________
(LAST NAME, Given Name; Print Clearly)

City & Province ___________ Date of Birth

E-Mail ____________ Home Telephone ( ) - _

Years at a Canadian high school ___ No. of chemistry courses at a Québec CÉGEP ___
Male  Canadian Citizen  Landed Immigrant  Visa Student 
Female  Passport valid until February 2020  Nationality of Passport ___________
Teacher __________________________ Teacher E-Mail_______________________
POLYMER CHEMISTRY
1. Polyethylene glycol (PEG) is a polymer formed via condensation polymerization which
is a form of step-growth polymerization. PEG is a hydrophilic molecule with applications
such as acting as a ligand for water insoluble nanoparticles to solubilize them into
aqueous solutions.

a) PEG is formed via a condensation polymerization using ethylene glycol (ethane-1,2-

diol) as a monomer. Draw the structure of ethylene glycol. 1 mark

b) Draw the structure of a dimer (two monomers attached) of PEG. 1 mark

c) Draw PEG represented in polymeric form with n units. 1 mark

The polydispersity index (PDI) is used to measure the distribution of sizes of polymers in
a given sample. It is calculated by the following formula:
𝑀𝑤
𝑃𝐷𝐼 =
𝑀𝑛
Where Mw is the weight average molecular weight and Mn is the number average
molecular weight. Mw is calculated by taking the sums of the squares of the weights of
each polymer unit and dividing by the sum of all the weights, whereas Mn is calculated by
taking the sums of all the weights and dividing by the number of polymers.
∑𝑁𝑖 𝑀𝑖2 ∑𝑁𝑖 𝑀𝑖
𝑀𝑤 = 𝑀𝑛 =
∑𝑁𝑖 𝑀𝑖 ∑𝑁𝑖

-2-
Below is a table of the weights of different polymeric units of PEG in a given sample.

Counts (N) Weights (M), g mol-1

2 502
4 546
6 590
3 634
1 1164

d) Calculate the PDI of the PEG sample. 2 marks

e) Calculate how many monomers were used to form the 1164 g mol-1 unit. 2 marks

-3-
A parameter used to show the extent of monomer polymerization is p. For example, p =
0.5 would signify 50% monomer polymerization. In the case of step-growth
polymerization, such as for PEG, p can be represented in the following ways with respect
to Mw and Mn.
𝑀𝑤 − 𝑀𝑜 𝑀𝑛 − 𝑀𝑜
𝑝= 𝑝=
𝑀𝑤 + 𝑀𝑜 𝑀𝑛
f) Find an expression for PDI in terms of only p. 2 marks

g) Calculate p for the sample of PEG based on your calculated PDI. 1 mark

h) What are the maximum and minimum values of PDI? 2 marks

PDImax =

PDImin =

-4-
ANALYTICAL CHEMISTRY
2. Ethylenediaminetetraacetic acid (EDTA) is a chemical of great industrial and medical
importance, due to its potency as a chelating agent for metals. EDTA binds to metals in
a 1:1 ratio. The structure of EDTA and the pKa values of its 4 carboxyl protons are given
below.

pKa1 = 2.0, pKa2 = 2.7, pKa3 = 6.1, pKa4 = 10.3

a) Which form of EDTA would you expect to predominate at neutral pH? Draw the
structure below. 2 marks

A 1.032g sample of iron ore containing both hematite (Fe2O3, M=159.688 g/mol) and
magnetite (Fe3O4, M=231.553 g/mol) is contaminated by metal A and metal carbonate
BCO3. The following procedure is carried out to determine the identity and quantity of
contaminants in the ore:

i. The sample is dissolved in excess concentrated HCl and chilled in an ice bath,
yielding a white precipitate of mass 0.099g with identity ACl2. The filtrate is boiled to
remove dissolved carbon dioxide and transferred to a 100.0 mL volumetric flask.
Distilled H2O is added to the mark. At this point, both Fe2+ and Fe3+ are present in
solution.
ii. A 25.0 mL aliquot of stock solution is titrated with 0.0970M KMnO4 under acidic
conditions, requiring 1.32 mL to reach endpoint.
iii. Excess copper metal is added to a second 25.0 mL aliquot of stock solution to
reduce any Fe3+ present in solution to Fe2+. Any remaining copper is filtered out, and the
titration is repeated, this time requiring 5.19 mL of 0.0970M KMnO4.
iv. A third 25.0 mL aliquot of stock solution is adjusted to pH 11, forming a white
precipitate of iron (II, III) hydroxide. The filtrate is collected and titrated with 0.182M
EDTA to a murexide endpoint of 2.38 mL.

-5-
b) Write and balance the redox equation for the reaction of KMnO4 with Fe2+ in acidic
solution to form Mn2+ and Fe3+. 1 mark

c) From step (ii), calculate the mass of magnetite in the ore sample. (Hint: Fe 3O4 is
equivalent to Fe2+Fe3+2O4) 2 marks

d) From steps (ii) and (iii), calculate the mass of hematite in the ore sample. 2 marks

-6-
e) From step (i), suggest a plausible identity for contaminant A, and determine the mass
of A in the ore sample. 2 marks

f) From step (iv) and your answers to the questions above, determine the identity of
contaminant B. If you did not get an answer for any one or more of (c), (d), or (e), use
0.147g for the mass of BCO3 in the ore (Note: may not give the same answer for the
identity of B). 2 marks

g) When CO2 is bubbled through the filtrate from step (iv) (pre-EDTA titration), a white
precipitate forms. Write the balanced chemical equation for the formation of this
precipitate. 1 mark

-7-
INORGANIC CHEMISTRY
3. Rhodium complexes are commonly used as organometallic catalysts. In the Monsanto
process, cis-[Rh(CO)2I2]- is used to catalyze the carbonylation of a methyl halide.

a) Assuming the same electronic state of Rh as above, find a formula for the charge of
the complex, n, in terms of a, b and c for the complex [Rha(CO)bIc]n. 2 marks

b) [Rh(CO)2I2]- has two isomers: cis and trans. Draw the two isomers (you do not need to
note which is cis and which is trans). 2 marks

c) How many valence d electrons does Rh have in cis-[Rh(CO)2I2]-? Hint: The 5s orbital
only contains 1 electron in Rhodium’s ground state electronic configuration. 2 marks

d) Draw and fill in a crystal field splitting diagram for cis-[Rh(CO)2I2]-. Assume that CO
and I- have similar electronic properties. 3 marks

e) Circle the correct answer. Cis-[Rh(CO)2I2]- is: 1 mark

Diamagnetic Paramagnetic Ferromagnetic

f) Starting from 0 to 10 inclusively, write down EACH number of valence d electrons that
would make cis-[Rh(CO)2I2]n diamagnetic assuming the same crystal field splitting
properties. 2 marks

-8-
ORGANIC CHEMISTRY
4. a) Draw or write reagents A, B, C, D, and E for the reaction scheme below. Include
any necessary conditions. Any aqueous work up is assumed and does not need to be
added. 5 marks

-9-
b) Draw the structures of F, G, H, I, J, and K for the reaction scheme below. 6 marks

c) Draw the structure of a potential product, L, based on the reaction scheme below.
Your answer CAN NOT be the same as the structure you drew for K. There is no box
for the answer, please use the space below. 1 mark

- 10 -
PHYSICAL CHEMISTRY
5. Criegee Intermediates, CH2OO, have attracted significant interest in recent years due
to their critical role in many atmospheric processes. The atmospheric fate of a Criegee
Intermediate is largely determined by its reactions with water, due to the high
concentration of water in the atmosphere. The following two step reaction and plot show
the reaction of the simplest Criegee Intermediate with the water monomer,

where k1 and k-1 are the forward and reverse rate constants for the formation of a weakly
bound complex, CH2OO⋯H2O, that then proceeds to the product, CH2(OH)OOH, with the
rate constant k2.
4 Transition State
2
CH2OO + H2O 2.82
Relative Energy (kcal /mol)

0
0
-2
-4
-6.53
-6
-8 CH2OO⋯H2O
-10
-40
-12 CH2(OH)OOH
-42
-14
-41.42
-16
Reaction Coordinate

a) Calculate the activation energy of the second step of (1). 1 mark

b) Calculate the overall reaction energy. 1 mark

- 11 -
The rate at which the product is formed is notated . Similarly, the
concentration of the weakly bound complex changes at a rate of . The
expressions for these two rates in terms of their rate constants are:

The steady state approximation assumes that the weakly bound complex reacts as
quickly as it is produced (the concentration is constant). This gives a second expression
for the rate of change of the weakly bound complex:

c) Using these expressions, solve for the rate at which the product is formed in terms of
only the initial reactants [CH2OO] and [H2O] and the rate constants k1, k-1, k2. 3 marks

d) For bimolecular reactions with an activated complex, we can often assume that the
forward step for formation of the activated complex is much slower than the backwards
step (k2 << k-1). This means k-1 + k2 ≈ k-1. Simplify your final expression from part c based
on this assumption. 1 mark

- 12 -
We can determine rate constants, like k2, with statistical mechanics and accurate
descriptions of a molecule’s energy levels. The following questions investigate the
vibrational energy levels of HCl. The simple harmonic oscillator is a common
approximation for the vibration of a diatomic molecule and follows Hooke’s Law. The
harmonic oscillator potential, V(l), is given below (l is the displacement of the H-Cl bond
from its equilibrium length, l0). The corresponding energy, En, for each of its vibrational
energy levels, n, is also given.

The bond stretching frequency, ν, is related to the force constant, k, and h is Plank’s
constant. As the displacements, l, grow larger, the harmonic-oscillator potential begins to
diverge from the true potential. A better approximation is given by the Morse potential:

where De is the dissociation energy of the molecule, β is a measure of the curvature of

V(l) around its minimum, and χe is the anharmonic constant. An example of these
potentials with energy levels, n, is shown in the figure below. The dotted lines correspond
to a harmonic potential and the solid to a Morse potential. (Note that exp is equivalent to
Euler’s number, e)

n=3

n=2

n=1

n= 0

l0 l

- 13 -
e) The ground state energy, n=0, of a molecule is E0. If the transition from n=0->2 for HCl
has energy E2->0 = E2 – E0 = 5668 cm-1, estimate the ground state energy of HCl using
the harmonic approximation. 2 marks

f) If E3->0 = 8347 cm-1, what should be the ground state energy of HCl using the harmonic
approximation? 1 mark

g) Your values from parts e and f should be different due to anharmonicity. Use E2->0 and
E3->0 to estimate the anharmonic constant, χe. 3 marks

-END OF PART C-
- 14 -
THE CANADIAN CHEMISTRY CONTEST 2019
PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)
All contestants should attempt this part of the contest before proceeding to Part B and/or Part C.
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

1) A solution is 0.0240 mol L-1 KI and 0.0146 mol L-1 MgI2. What volume of 5) The melting point of CaS is higher than that of KCl. Explanations for this
water should be added to 100.0 mL of this solution to produce a observation include which of the following?
solution with [I-] concentration of 0.0500 mol L-1? I. Ca2+ is more positively charged than K+.
A) 106.4 mL B) 53.2 mL C) 26.6 mL D) 13.3 mL E) 6.4 mL II. S2– is more negatively charged than Cl–.
. III. The K+ ion is smaller than the Ca2+ ion.
2) The boiling points of the compounds acetic acid (CH3COOH), 1-pentanol
(C5H11OH), dibutyl ether (C8H18O) and dodecane (C12H26) increase in A) II only B) I and II only C) I and III only
that order. Which of the following statements provides the best D) II and III only E) I, II, and III
explanation for this increase?
6) Fluorine is the most electronegative element on the periodic table. As a
result it always forms polar bonds with other non-metals. Despite this,
A) The London dispersion forces increase
which of the following fluorine containing compounds would be a non-
B) The hydrogen bonding increases
polar molecule?
C) The dipole-dipole forces increase
D) The chemical reactivity increases A) SF4 B) PF3 C) IF5 D) BrF3 E) XeF4
E) The number of carbon atoms increases
7) Ronald James Gillespie, who developed Valence Shell Electron Pair
3) Health Canada recommends that women between the ages of 12 and 45 Repulsion (VSEPR) theory, isolated the superacid fluorosulfuric acid
consume 400 micrograms of folic acid (C19H19N7O6) per day, which
(HSO3F) when he combined fluorinated compounds with concentrated
reduces the risk of neural tube defects during pregnancy. How many
sulfuric acid, creating brightly coloured solutions. Which of the
moles of folic acid are equivalent to 400 micrograms?
following best describes the molecular shape of fluorosulfuric acid, as
A) 1.10 mmol B) 0.177 mol C) 0.906 mol predicted by VSEPR theory?
D) 0.906 mmol E) 9.06 x 10-7 mol
A) See saw B) Trigonal bipyramidal C) Tetrahedral
4) An unknown amino acid contains 9.5 % nitrogen by mass as determined D) Square planar E) Trigonal pyramidal
by elemental analysis. Which of the following could be the unknown
amino acid?
8) Vinegar used as a cooking ingredient, or in pickling, is a solution of 5%
acetic acid (CH3COOH) by mass in solution with water. The pKa= 4.76
A) arginine C6H14N4O2 B) cysteine C3H7NO2S
C) histidine C6H9N3O2 D) glutamic acid C5H9NO4 for acetic acid at 25C. Evaluate the pH of vinegar at 25 C.
E) glycine C2H5NO2
A) 4.80 B) 4.15 C) 2.92 D) 2.42 E) 2.24
CCC 2019 page 2 of 4

9) The ionization energies for period 3 element X are listed in the table 11) Given the following electrochemical cell data:
below. Cell 1 Cd(s) | Cd2+ (1.0M) || Cu2+ (1.0M) | Cu(s) Eo = +0.74 V
Cell 2 Zn(s) | Zn2+ (1.0 M) || Cu2+ (1.0 M) | Cu(s) Eo = +1.10 V
Cell 3 Zn(s) | Zn2+ (1.0 M) || Cd2+ (1.0 M) | Cd(s)
Ionization Energies for element X (kJ mol-1)
First Second Third Fourth Fifth Determine the standard cell potential for Cell 3.
580 1,815 2,740 11,600 14,800
A) – 0.36 V B) 0.36 V C) –1.84 V
D) –0.18 V E) 0.18 V
Based on the data, which statement about element X is FALSE?
12) Lead (II) sulfate can decompose into lead (II) sulfite and oxygen gas
A) Its most common oxidation state is +3 when heated. If the reaction generates 2.25 g of oxygen gas, what mass
B) It is displaced from aqueous solution by copper metal of lead (II) sulfate reacted? Assume 100% yield in this reaction.
C) It is the most abundant metal in the Earth’s crust
D) Its oxide is insoluble in water A) 42.6 g B) 21.3 g C) 20.2 g D) 10.7 g E) 4.50 g
E) It is a lustrous metal
13) A student combines 75 mL of 0.500 mol L-1 hydrochloric acid with
10) Stavzor (structure below) is a medication primarily used to treat epilepsy and 55 mL of 0.125 M KOH. What is the pH of the resulting solution?
bipolar disorder.
A) 0.30 B) 0.39 C) 0.63 D) 1.51 E) 7.00
HO O
14) A system undergoes a reversible cyclic process and proceeds through
Stavzor a series of thermodynamic processes, exchanging heat and work with
its surroundings and ultimately returning to its original state. Which
one of the following statements is true? Assume that the surroundings
A well-known substance with a characteristic odour of bananas (A) is a are much, much larger than the system.
constitutional isomer of Stavzor. Which of the following is a possible
structure for A? A) Ssurroundings > 0 B) q > 0 C) q < 0 D) q = w = 0 E) S > 0

O OH O O
O 15) The thermite reaction is the reaction of aluminum metal and iron (III)
oxide:
(a) (b) (c) O 2 Al (s) + Fe2O3 (s)  Al2O3 (s) + 2 Fe (s) H = –852 kJ

A teacher does a demonstration with 1.00 mol of iron (III) oxide and
O O O 2.00 mol of aluminum metal both initially at 25.0 C. If the combined
(d) (e) specific heat of the products is 0.800 J g-1 C-1 over a wide range of
O
temperatures, what is the final temperature of the products?

A) 3550C B) 4960 C C) 5010 C D) 6470 C E) 6500C

CCC 2019 page 3 of 4

16) The compound acetanilide is important in the industrial synthesis of 18) Given the following set of equilibria and their respective constants
several dyes. Acetanilide (mol. wt. = 135.16) can be made in the
laboratory by a reaction between aniline and excess acetic anhydride NH4+ ⇌ H+ + NH3 Ka = 5.6 x 10–10
which has a yield of 61.5%: H2CO3 ⇌ H+ + HCO3– Ka1 = 4.2 x 10–7
NH2 HCO3–⇌ H+ + CO32– Ka2 = 2.4 x 10–8
O
O O what would the equilibrium constant be for the reaction below?
+
N
O H2CO3 + 2 NH3 ⇌ (NH4)2CO3 K=?
H
aniline acetic anhydride acetanilide A) 1.8 x 10–5 B) 4.4 x 10–7 C) 9.0 x 10–6
D) 3.2 x 104 E) 3.1 x 10–5
Aniline and acetic anhydride are both liquids which have densities of
1.219 g mL-1 and 1.082 g mL-1 respectively.

What volume of aniline was used in this reaction if the recorded mass of 19) The subshell filling order used for the quantum mechanical model of
acetanilide product was 7.14 g? the atom is an approximation of the relative subshell energies, which
assumes the energies remain fixed. However, there are exceptions to
A) 4.03 mL B) 9.75 mL C) 4.92 mL the Aufbau Principle. Which of the following is the correct ground state
D) 5.99 mL E) 6.56 mL configuration of an element found on the periodic table?

17) One of the Twelve Principles of Green Chemistry is that “synthetic

A) [Ar] 4s1 3d5 B) [Ar] 4s2 3d4 C) [Ar] 4s2 4d4
methods should be designed to maximize the incorporation of all
materials used in the process into the final product”. One way to D) [Ar] 4s2 4p4 E) [Ar] 4s1 4p5
consider this is to calculate the atom economy (AE) of a chemical
reaction where AE is defined as follows:

𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑑𝑒𝑠𝑖𝑟𝑒𝑑 𝑝𝑟𝑜𝑑𝑢𝑐𝑡 20) A vessel contains 2.50 mol of O2 gas, 0.50 mol of N2 gas and 1.00 mol of
𝑎𝑡𝑜𝑚 𝑒𝑐𝑜𝑛𝑜𝑚𝑦 = × 100% CO2 gas. The total pressure is 200 kPa. The partial pressure exerted by
𝑚𝑜𝑙𝑒𝑐𝑢𝑙𝑎𝑟 𝑚𝑎𝑠𝑠 𝑜𝑓 𝑎𝑙𝑙 𝑟𝑒𝑎𝑐𝑡𝑎𝑛𝑡𝑠
the O2 in the mixture is:

The atom economy of the reaction in the previous question (#16) is: A) 25 kPa B) 50 kPa C) 100 kPa D) 125 kPa E) 150 kPa
A) 61.5% B) 69.2% C) 100% D) 68.9% E) 74.4%
CCC 2019 page 4 of 4

21) The O2 (g) produced in the decomposition of 3.275 g mixture of 23) For the reaction H2 (g) + I2 (g) ⇌ 2 HI (g) H = +52.96 kJ.
potassium chlorate and potassium chloride which is 65.82% KClO3 by Which of the following statement(s) is/are correct?
mass is collected over water at 21.0 C. Assume ideal gas conditions. If
atmospheric pressure is 753.5 mmHg, water vapour pressure at 21.0C I. The heat of formation of 1 mol of HI is +26.48 kJ
is 18.7 mmHg, once the pressure in the gas collection vessel was II. As the temperature increases, the reaction will proceed to the
equalized with atmospheric pressure, how many milliliters of O2 gas right
would be produced according to the reaction: III. As the pressure increases, the reaction will proceed to the
right
2 KClO3 (s)  2 KCl (s) + 3 O2 (g)
A) I only B) I and II only C) I, II and III
B) II and III only E) III only

24) Calculate G at 25 C for the reaction given the data below
KClO3
4 HCl (g) + O2 (g)  2 Cl2 (g) + 2 H2O (g) H = –114.4 kJ
O2 𝑜
𝑆𝐶𝑙 2
= 223.0 J mol-1 K-1 𝑆𝐻𝑜2 𝑂 = 188.7 J mol-1 K-1,
𝑆𝑂𝑜2 = 205.0 J mol-1 K-1 𝑜
𝑆𝐻𝐶𝑙 = 186.8 J mol-1 K-1

A) + 14.4 kJ B) –111.18 kJ C) + 3105.6 kJ

D) + 38 kJ E)– 76.0 kJ

A) 130 mL B) 439 mL C) 563 mL 25) For the reaction 2 NO (g) + Cl2 (g)  2 NOCl (g) the table below
D) 658 mL E) 1320 mL provides experimental data for 3 different reactions.

After equilibrium is established, which container would have the largest

concentration of CO (g) End of Part A of the contest
Go back and check your work
A) 1 B) 2 C) 3 D) 4 E) 5
Rubric guideline for evaluating the CCC (Part B) essay topics
For a total mark out of 20 points

Criteria 4 marks 3 marks 2 marks 1 mark

Format The essay is written with an engaging, The essay has an The introduction is partially The essay is
(mark x 1) clear introduction. For the lab design interesting, clear developed. The lab format is disorganized and/or
the purpose, materials, procedure, introduction. The lab evident but some of the sections confusing and simplistic
calculations, analysis, errors and format is evident but not are missing. For the essays, at
conclusion are comprehensive (in comprehensive. For the least one point is well
some cases not all sections will be essays, some points are developed. There is a lack of
required), show insight, organization, developed well. A development of ideas and the
clarity and understanding. For the conclusion paragraph conclusion is simplistic/
essays, (3) points are clearly developed brings the essay to a close confusing/ too general
and a concluding paragraph brings the
essay to a logical close.
Topic The discussion of the essay/lab topic The discussion of the The discussion of the essay/lab The discussion of the
synthesis is comprehensive, with careful essay/lab topic is good, topic is fair, with minimal essay/lab is inadequate.
(mark x 3) analysis of ideas included in the with attention to items attention to items queried in the
question queried in the question question
Extension/ Unexpected, original or new points are There is an attempt to Any extensions relate poorly or No attempt to make
Originality introduced in the essay/lab. These make new connections are very unclear. There is little new connections is
/Depth extensions are clearly explained and but some original thought in the evident and the essay
(mark x 1) relate well to the topic/lab. The misunderstandings are essay/lab. The essay/lab does not demonstrate a
essay/lab demonstrates a deep evident. The essay/lab demonstrates some depth of knowledge.
understanding of the topic demonstrates a good understanding of the topic.
understanding of the
topic.
Total /20
THE CANADIAN CHEMISTRY CONTEST 2018
PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)
All contestants should attempt this part of the contest before proceeding to Part B and/or Part C.
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

1) Sodium hydroxide (NaOH) is commonly used in high school labs. 3) What is the mole percent of a solution of ethanol (C2H5OH) which
NaOH is a WHMIS category 1 health hazard causing severe eye, consists of 71.0 g of ethanol for every 12.8 g of water present?
skin and respiratory tract effects. NaOH is hygroscopic and
readily absorbs moisture from the air. Any prepared solution of A) 2.17 % B) 12.3 % C) 31.6 %
NaOH should be standardized to determine its precise concentration. D) 68.4 % E) 84.7 %
You have the glassware V, W, X, Y, Z below and solid pellets of NaOH.
100 mL 125 mL 4) A 2.0 L balloon initially holds 3.0 mol of helium. When 3.0 mol of helium
are added, the volume of the balloon increases to 4.0 L and the
50 mL
temperature remains unchanged. Which expression correctly
10 mL
describes the final pressure of the system in terms of the initial
pressure, P? Assume Ideal Gas behaviour.
100 mL

A) P B) 2P C) 3P D) 4P E) 6P
V W X Y Z
Which of the choices provides the safest, most efficient method of 5) A compound is composed of element X and hydrogen. Analysis shows
preparing exactly 100.0 mL NaOH of approximately 1M before the compound to be 79.89 % X by mass, with three times as many
standardizing the solution with 0.500 M oxalic acid (C2O4H2)? Assume hydrogen atoms as X atoms per molecule. Which element is element X?
the NaOH solution is mixed thoroughly once prepared.
A) He B) C C) N D) P E) S
A) Filling V with approximately 50 mL water, adding 4.0 g NaOH,
diluting to precisely 100 mL in V. 6) To increase strength and hardness when forging knives and blades, hot
B) Filling W with approximately 50 mL water, adding 4.0 g NaOH and steel can be quenched by rapidly cooling in water. A 454 g steel blade is
diluting to 100 mL in W. heated to a uniform temperature, and then quenched in 2000 mL of
C) Placing 4.0 g NaOH in X then adding 100 mL of water to X using Y. 25.0 oC water. If the steel blade loses 173.7 kJ of heat during the
D) Placing 4.0 g NaOH in W then adding 100 mL of water to W using Z. quenching process, what is the final temperature of the water? The
E) Filling X with precisely 50 mL of water using Z, adding 4.0 g of NaOH specific heat capacity of water is 4.18 J g–1 oC–1. Assume no water
and adding an additional 50 mL of water using Z. evaporates during the quenching process.
2) Vitamin C (C6H8O6) supplements often come in 500 mg tablets. If a A) 16.9 oC B) 20.7 oC C) 41.9 oC D) 45.8 oC E) 91.5 oC
person consumes one 500 mg tablet of Vitamin C, how many moles of
Vitamin C would they be consuming?

A) 2.84 x 10-3 B) 8.81 x 10-2 C) 1.00

D) 2.84 E) 88.1
CCC 2018 page 2 of 4

7) Table 1: Successive Ionization Energies of 3rd Period Elements 10) Tigan (structure below) is an antiemetic drug used to prevent nausea
and vomiting. It is often prescribed for patients with gastroenteritis,
Element IE1 IE2 IE3 IE4 IE5 medication-induced nausea, and other illnesses.
(kJ –1 mol –1) (kJ –1 mol –1) (kJ –1 mol –1) (kJ –1 mol –1) (kJ –1 mol –1)
O

V 787 1577 3231 4356 16091 N

O
H
N
W 738 1451 7733 10540 13630 O O

Tigan O
X 1251 2297 3822 5158 6540

Y 496 4562 6912 9543 13353 Which of the following functional groups are present within Tigan?

Z 578 1817 2745 11575 14830 A) amine, ether, amide B) amine, ketone, ether, alcohol
C) ether, aldehyde, amine D) alcohol, amine, ether, amide
E) ketone, amine, ether
Based on this information, which of the following statements is FALSE?
11) How many carbon (C) and hydrogen (H) atoms are present in a
A) Y is sodium B) X has the smallest radius
molecule of Tigan?
C) W is an alkaline earth metal D) Z forms the largest cation
E) V is a semi-metal
A) 21 C and 28 H atoms B) 21 C and 27 H atoms
C) 16 C and 28 H atoms D) 20 C and 28 H atoms
8) Hydrofluoric acid reacts with potassium hydroxide according to the net
E) 21 C and 29 H atoms
ionic equation:
HF (aq) + OH– (aq)  F– (aq) + H2O (l) 12) Which of the following would increase the Keq of the reaction below?

If 5.0 mL of 1.0 M KOH are added to 25.0 mL of 2.0 M HF, what is the pH HCO3– (aq) + H3O+(aq) ⇌ H2CO3(aq) + H2O(l)
of the resulting solution? The Ka of HF is 7.2 x 10–4.
A) Increasing the pH B) Decreasing the pH C) Adding water
A) 1.42 B) 1.48 C) 1.66 D) 2.19 E) 2.84 D) Adding H2CO3 E) None of the options
provided
9) For a reaction A + B —> Products, the rate law is: rate= k[A][B]2. For
containers with the same volume, which mixture would have the 13) In 1962, at the University of British Columbia, Neil Bartlett shattered
highest rate of reaction according to this rate law? The legend indicates conventional chemistry wisdom and synthesized xenon tetrafluoride,
which molecule is A and which is B. the first binary compound of a noble gas. Which of the following
Legend statements is/are true about a molecule of xenon tetrafluoride?

A) B) C) D) E) I) The molecule has no lone pairs on the central atom

II) The molecule has a tetrahedral geometry
III) The molecule has no net molecular dipole

A) I only B) II only C) III only D) II and III E) I, II and III

CCC 2018 page 3 of 4

17) Use the information provided below to calculate the enthalpy of

14) For the titration of HNO3 reaction when one mole of chlorine trifluoride gas decomposes into
with KOH, which of the one mole of chlorine monofluoride gas and one mole of gaseous
following receiving flasks fluorine.
best depicts the ions present 2 ClF(g) + O2(g)  Cl2O(g) + F2O(g) ΔH = + 167.4 kJ
at the endpoint as indicated
on this titration curve? 2 ClF3(g) + 2 O2(g)  Cl2O(g) + 3 F2O(g) ΔH = + 341.4 kJ

3
3 F2O (g)  3 F2(g) + O2(g) ΔH = + 65.1 kJ
A) B) C) D) E) 2

A) -217.4 kJ B) +25.0 kJ C) +68.4 kJ D) +108.7 kJ E) 573.9 kJ

18) Consider the following reaction, where the starting compound is

treated with an unknown reagent over a catalytic surface to form the
product:

?
catalyst
15) What is the pH of a solution created by mixing 1000.0 mL of 0.120 M
HNO3 (aq) with 250.0 mL of 0.750 M HBr (aq)?
Which two terms can be used to describe this process?
A) 1.268 B) 0.000 C) 0.060 D) 0.512 E) 0.609
A) hydrogenation, elimination B) hydration, addition
C) hydrogenation, substitution D) hydrogenation, addition
16) The smell often associated with public swimming pools comes from
E) hydration, substitution
chloramines. The reaction of hypochlorous acid with ammonia from
human urine will produce monochloramine (NH2Cl) as follows:
19) A quantity of solid material weighing 6.445 g was obtained from a
HOCl(aq) + NH3(aq) ⇌ NH2Cl(aq) + H2O(l) Keq = 1.47 x 1011 hazardous waste facility. A 1.545 g sample of this material was
analyzed for barium content by dissolving in water and then adding
One part per million (ppm) is a mg L–1. A typical public swimming sodium sulfate. The insoluble barium sulfate precipitate was dried, and
pool volume (750,000 L) contains 75.0 L of urine. The concentration a total of 73.8 mg of BaSO4 was collected. What percentage by mass of
of ammonia in 1 L of urine is 0.200 M. If the concentration of the sample is barium?
hypochlorous acid in pool water is 1.00 ppm, determine the
concentration (in ppm) of monochloramine (NH2Cl) in a typical public A) 0.281 % B) 0.674 % C) 2.81 % D) 4.02 % E) 6.74 %
swimming pool. Assume the mass of 1 L of pool water is 1 kg.
20) Which of the following accurately represents a trend in atomic radius?
A) 1.91 B) 1.64 C) 1.03 D) 1.00 E) 0.98
A) F > Cl > Br B) F > O > N C) Cl- > Na+ > Mg2+
D) Ca2+ > K+ > Ca E) O2- > S2- > Cl
CCC 2018 page 4 of 4

Power source
21) 96.5% of water available on Earth is sea water. 23) Another way to make diamonds in the lab is by converting graphite to
Desalination of seawater could provide a solution to the diamond. At 2000 K and 200 000 atm:
global fresh water crisis. There are many challenges
that chemists face in achieving desalination. Given the C (graphite) ⇌ C (diamond); ΔG = −10 kJ mol-1, ΔS = −10 J K−1 mol−1
half reactions below and the setup of the electrolytic
cell to the right, what would happen with an Which of the following is a good approximation of the equilibrium
applied potential difference from the power temperature for the reaction at 200 000 atm if enthalpy and entropy
source? are assumed to be temperature independent?

Students will answer TWO questions as follows: all students must answer the experimental design question 1;
students have the choice between answering either question 2 or question 3. For each question, students should
write a scientific essay including appropriate equations, formulae and diagrams. Each essay is of equal value. Allocate
approximately equal time to each question. Scorers will consider the accuracy and quality of the information and the
presentation of the responses. A clear, concise, well-organized piece of written work will be rated more highly than a
long rambling one. A scientific calculator is allowed. No phones or communication devices are allowed.

1) Experimental Design: Reaction Rates (mandatory question)

The hypochlorite ion OCl– is important for disinfecting water for drinking, water in pools and for removing stains from
clothing. The decomposition of hypochlorite can occur via the two mechanisms below:
Mechanism 1 Mechanism 2
2ClO– (aq) 2 Cl– (aq) + O2 (g) (very slow) 2 CoO(s) + ClO-(aq)  Co2O3 (s) + Cl-(aq) (slow)
Co2O3(s) + ClO- (aq)  Co2O3  ClO- (adsorbed) (fast)
Co2O3  ClO- (adsorbed)  2CoO(s) + Cl-(aq) +O2 (g) (fast)

Transition metal compounds are good catalysts for the decomposition of the hypochlorite ion. Design an experiment
based on either mechanism to determine the conditions that would lead to the fastest decomposition of sodium
hypochlorite in solution. Start your lab procedure with an introduction that demonstrates your understanding of the
factors that would affect the rate of this reaction. In your laboratory design, provide a materials list and a clear,
numbered, step-by-step procedure. Provide tables of observation to demonstrate how you would collect your data to
assess the conditions which would lead to the fastest rate of decomposition. Identify possible sources of error and
how you would minimize them. Assume you have access to all glassware and equipment found in a typical high school
laboratory.
2) Organic Chemistry
Many students in Canada study Organic Chemistry. The study of organic chemistry focuses primarily on carbon,
hydrogen, oxygen and nitrogen. Why is organic chemistry important if it is based on only 4 of the 118 elements on the
periodic table? In your answer, demonstrate an understanding of the central concepts in organic chemistry. Highlight
some interesting characteristics of several functional groups and their chemical properties. Highlight trends in the
physical properties of different groups of organic compounds, why differences in physical properties exist and how
the physical and chemical properties of organic compounds can be applied to everyday life.

3) Chemistry
Linus Pauling (1901-1994) was the recipient of the 1954 Nobel Prize in Chemistry and the 1962 Nobel Peace Prize. He
worked enthusiastically on determining the nature of chemical bonds, the structure of molecules and crystals, and he
introduced the concepts of electronegativity, hybridization, resonance as well as many fundamental concepts in
molecular biology. He also worked tirelessly trying to prevent nuclear testing during the Cold War. He stated: “every
aspect of the world today – even politics and international relations – is affected by chemistry”. Discuss the
importance of chemistry today in solving and influencing some of the world’s biggest problems. Use two or three
specific examples of the influence of chemistry in your discussion.
THE CANADIAN CHEMISTRY CONTEST 2018
for high school and CEGEP students
(formerly the National High School Chemistry Examination)

PART C: CANADIAN CHEMISTRY OLYMPIAD

Final Selection Examination 2018
Free Response Development Problems (90 minutes)
This segment has five (5) questions. While students are expected to attempt all questions for a
complete examination in 1.5 hours, it is recognized that backgrounds will vary and students will
not be eliminated from further competition because they have missed parts of the paper.

— PLEASE READ — PART A ( )

Correct Answers
1. BE SURE TO COMPLETE THE INFORMATION REQUESTED AT THE
BOTTOM OF THIS PAGE BEFORE BEGINNING PART C OF THE
EXAMINATION. 25 x 1.6 = ......... /040

2. STUDENTS ARE EXPECTED TO ATTEMPT ALL QUESTIONS OF

4. .................... /012
4. ONLY NON-PROGRAMMABLE CALCULATORS MAY BE USED ON
THIS EXAMINATION. 5. .................... /012

5. NOTE THAT A PERIODIC TABLE AND A LIST OF SOME PHYSICAL

City & Province ___________ Date of Birth

E-Mail ____________ Home Telephone ( ) - _

Years at a Canadian high school ___ No. of chemistry courses at a Québec CÉGEP ___
Male  Canadian Citizen  Landed Immigrant  Visa Student 
Female Passport valid until February 2019 Nationality of Passport ___________
Teacher __________________________ Teacher E-Mail_______________________
ANALYTICAL CHEMISTRY
1. a) Phosphoric acid, H3PO4, is a triprotic acid with the following acid dissociation
constants: Ka1 = 7.5 * 10-3, Ka2 = 6.2 * 10-8, and Ka3 = 2.2 * 10-13. If a solution of
phosphoric acid initially had [H3PO4] = 0.0403 M, calculate [PO43-] at equilibrium.
5 marks

-2-
b) Given the data below at room temperature, estimate the value of the missing
equilibrium constant. 3 marks
MX ⇌ M+ + X- K1 = 4.005
2+
RX2 ⇌ R + 2X - K2 = 0.6140
2MX + R2+ ⇌ RX2 + 2M+ K3 = ?

c) Using the K values above, calculate the Gibbs free energy of each reaction at room
temperature. 2 marks

d) Calculate the Gibbs free energy of the third reaction using the Gibbs free energies of
the first two reactions and compare it with the value you obtained in part c). Are they
different? Similar? Explain why in up to three sentences. 2 marks

-3-
ORGANIC CHEMISTRY
2. Sertraline is a potent pharmaceutical agent for the treatment of depression. It is sold
under the name Zoloft and belongs to the class of antidepressants known as selective
serotonin reuptake inhibitors (SSRI). Approved for medical use in 1991, it is one of the
most prescribed psychiatric medications. The structure is shown below.

Sertraline can be prepared according to the following scheme:

a) Draw the structures of intermediates A, B, C and D in the boxes below. 4 marks

A B C D

-4-
b) Provide the reagents X, Y, Z below. 1.5 marks

X Y Z

c) Circle all the stereocenters in sertraline. State how many stereoisomers of sertraline
exist. 2 marks

d) Circle the two most acidic sites in the molecule depicted below. 1 mark

e) Deprotonation results in the formation of an enolate. There are two possible enolates.
The reaction conditions dictate which enolate will form. Draw the corresponding enolate.
1.5 marks

f) Circle the correct stereochemical marker of the molecule below. 0.5 marks

R or S (CIRCLE ONE)

g) Using the template provided, draw the corresponding Newman projection along the
C2 - C3 bond. 1.5 marks

-5-
BIOLOGICAL CHEMISTRY
3.

DNA and RNA comprise of connected nucleobases: adenine, cytosine, guanine,

thymine, and uracil as shown above. Many genetic disorders are caused by
trinucleotide repeats. Myotonic dystrophy is caused by a trinucleotide repeat of the
following trinucleotide.

a) Write the code (e.g. 5’ – AAA – 3’) that

corresponds to the trinucleotide. 1 mark

b) Write the complementary DNA sequence. 1 mark

c) Write the mRNA sequence that would be

transcribed from the initial trinucleotide. 1 mark

d) Draw the hydrogen bonding between uracil and its base pair on the template below.
3 marks

e) Circle the atom(s) that participate as Lewis base(s) in uracil on the template above.
1 mark

-6-
f) DNA and RNA can undergo autohydrolysis. Below is an example of a section of a
RNA strand and its product after autohydrolysis.

Propose a potential catalyst for this reaction and explain your reasoning in up to two
sentences. 1 mark

g) If the k of autohydrolysis for DNA is ~2 x 10-13 s-1, assuming first order kinetics,
calculate the half-life of DNA in years. 2 marks

h) Suppose the oxygen atoms in the above RNA strand were isotopically marked. What
would happen to the rate of autohydrolysis? Explain your reasoning in up to two
sentences. 1 mark

i) If the free energy of the products of autohydrolysis are lower than that of the RNA,
draw an uncatalyzed AND a catalyzed free energy diagram of the reaction. 2 marks

-7-
INORGANIC CHEMISTRY
4. Vanadium was first discovered in 1830 and was named after the Scandinavian
goddess of beauty, due to the striking range of colors which can be found in vanadium-
containing compounds. One group of these colorful compounds are the metal aquo
complexes formed from vanadium ions in aqueous solutions, including the lilac-colored
[V(H2O)6]2+.

a) What is the geometry around Vanadium in [V(H2O)6]2+? 1 mark

b) What is the electron configuration of the Vanadium (II) ion in [V(H2O)6]2+? 1 mark

c) What is the Lewis acid in [V(H2O)6]2+? 1 mark

The d-orbitals of transition metals like Vanadium are degenerate when observed in
individual atoms, but when transition metal ions are bound to ligands in complex ions,
the d-orbital electrons repel the lone pair electrons of the ligands. As a result, d-
electrons closer to the ligands will be higher in energy than d-electrons further from the
ligands, breaking degeneracy of the d-orbitals. This is the basic concept behind Crystal
Field Theory and crystal field “splitting” of orbitals.

d) Draw the electron configuration diagram for the d-orbitals and d-electrons of V2+ in
[V(H2O)6]2+ with crystal field splitting. 2 marks

e) Will the crystal-field splitting parameter Δ be larger or smaller in [V(H2O)6]3+

compared to [V(H2O)6]2+? 1 mark

Larger Smaller (CIRCLE ONE)

-8-
f) Assuming the same metal ion and other conditions, will the crystal-field splitting
parameter Δ be larger or smaller with CN- ligands compared to H2O ligands? 1 mark

Larger Smaller (CIRCLE ONE)

The complex ion [Co(CN)6]3- follows the same crystal field splitting pattern as
[V(H2O)6]2+. The crystal-field splitting parameter Δ is 4.2 eV and the spin pairing energy
of the Co (III) ion is 3.5 eV.

g) Draw the electron configuration diagram for the d-orbitals and d-electrons of Co3+ in
[Co(CN)6]3- with crystal field splitting. (3 marks).

h) Is this a high spin configuration or a low spin configuration? 1 mark

Low spin High spin (CIRCLE ONE)

i) What is the wavelength in nm of a photon that [Co(CN)6]3- would readily absorb?

2 marks

-9-
PHYSICAL CHEMISTRY
5. Metal X has been known to humanity for at least 5000 years, mostly in its silvery-
white metallic tetragonal β-form. The unit cell of this β-form is shown in the picture
below.

a) Identify X given that the density of β-X is 7.29 g/cm3 and its unit cell contains 4 atoms
of X and its parameters are a=0.583 nm and c=0.3181 nm. 3 marks

At low temperature this metal undergoes a phase transition to face-center cubic α-form.
b) Draw a unit cell of the α-X and indicate the number of atoms in the unit cell. 2 marks

c) Atomic radius of X is known to be 0.182 nm. Find the density of α-X. 2 marks

- 10 -
As a result of this phase transition, ductile and dense metallic β-X turns to brittle α-X.
Among non-chemists this transition is known as X pest, since the silvery white metal
tarnishes and visible cracks appear on its surface.
Allegedly, it was one of the reasons for failure of the first expedition to South Pole (lead
in 1910 by Robert Scott), since food and water containers were affected.

d) The phase diagram of X is displayed below. Estimate the temperature at which β-X
turns to α-X on Earth. Is it reasonable to blame X-pest based on your estimate? 1 mark

- 11 -
Element X has the largest number of stable isotopes at 10 due to its nuclear stability. Its
heaviest known isotope only has a half-life of 408 ns. Praseodymium, a different
element, has only one known stable isotope, Pr-141.

e) Write down the electron configuration of praseodymium in its ground state. 1 mark

f) If Pr-122 has a half-life of 0.5 s, and there was initially a mixture of 20% Pr-141 and
80% Pr-122, what would be the atomic weight of Pr before and after 11.2 s has passed?
2 marks

-END OF PART C-
- 12 -
THE CANADIAN CHEMISTRY CONTEST 2018
PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)
All contestants should attempt this part of the contest before proceeding to Part B and/or Part C.
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

A) 2.84 x 10-3 B) 8.81 x 10-2 C) 1.00

D) 2.84 E) 88.1
CCC 2018 page 2 of 4

V 787 1577 3231 4356 16091 N

O
H
N
W 738 1451 7733 10540 13630 O O

Tigan O
X 1251 2297 3822 5158 6540

Y 496 4562 6912 9543 13353 Which of the following functional groups are present within Tigan?

A) B) C) D) E) I) The molecule has no lone pairs on the central atom

II) The molecule has a tetrahedral geometry
III) The molecule has no net molecular dipole

A) I only B) II only C) III only D) II and III E) I, II and III

CCC 2018 page 3 of 4

17) Use the information provided below to calculate the enthalpy of

3
3 F2O (g)  3 F2(g) + O2(g) ΔH = + 65.1 kJ
A) B) C) D) E) 2

A) -217.4 kJ B) +25.0 kJ C) +68.4 kJ D) +108.7 kJ E) 573.9 kJ

18) Consider the following reaction, where the starting compound is

treated with an unknown reagent over a catalytic surface to form the
product:

Na+ (aq) + e–  Na (s) E = –2.71 V A) Teq = 2000 K B) Teq = 3000 K C) Teq = 1000 K
2H2O (l) + 2e–  H2 (g) + 2OH– (aq) E = –0.83 V D) Teq = 4000 K E) Teq = 100 K
O2 (g) + 4H+ (aq) + 4e–  2H2O (l) E = +1.23 V
24) Over 80% of global methanol (CH3OH) production is converted into
Cl2 (g) + 2e–  2Cl– (aq) E = +1.36 V further synthetic chemicals. Consequently, methanol is an economically
significant chemical compound. Methanex, a Vancouver-based company,
A) With 1.35 V, the cell produces Na at the cathode and Cl2 at the is the world’s largest producer and distributor of methanol. Methanol is
anode produced according to the following balanced chemical reaction:
B) With 1.35 V, the cell produces Na at the anode and Cl2 at the
cathode CO(g) + 2H2 (g) ⇌ CH3OH (g)
C) With 4.07 V, the cell produces Na at the cathode and Cl2 at the
anode Given initial partial pressures of PCO = 26 bar and PH2 = 65 bar, and an
D) With 2.06 V, the cell produces H2 at the anode and H2O at the equilibrium partial pressure of PCH3OH = 16 bar, determine Kp. Assume
cathode constant container volume and ideal gas behaviour.
E) With 2.06 V, the cell produces H2 at the cathode and O2 at the
anode A) 1.5 x 10-4 B) 6.7 x 10-4 C) 1.5 x 10-3
D) 3.3 x 10-2 E) 4.8 x 10-2
22) The market for lab-made diamonds is growing. Chemists can create
diamonds identical to mined diamonds by using chemical vapour 25) A chemist creates one litre of buffer solution by mixing unequal
deposition in which methane decomposes in the presence of a volumes of 1.0 M acetic acid (Ka = 1.74 x 10-5)
hydrogen catalyst and plasma. If this methane decomposition reaction and 1.0 M sodium hydroxide to obtain a
were possible at 298 K, what would be the Gibbs Free Energy ( G) of solution with the ratio of solution particles in
the lab-made diamond synthesis process indicated below (in kJ mol-1)? the diagram to the right. What is the pH of
the buffer solution?
CH4 (g) ⇌ C (diamond) + 2H2 (g)
A) 4.33 B) 4.54 C) 4.76
Compound CH4 (g) C (diamond) H2 (g) D) 4.98 E) 5.19
Hf (kJ mol-1) -74.87 1.897 0
S (J K-1 mol-1) 186.1 2.377 130.6
End of Part A of the contest
Go back and check your work
A) -23.0 B) 23.0 C) 53.7 D) -53.7 E) 92.6
Rubric guideline for evaluating the CCC (Part B) essay topics (out of 20 marks)
Criteria 4 marks 3 marks 2 marks 1 mark
Format The essay is written with an engaging, The essay has an interesting, The introduction is partially The essay is disorganized
(mark x 1) clear introduction. For the lab design clear introduction. The lab developed. The lab format is and/or confusing and
the purpose, materials, procedure, format is evident but not evident but some of the sections simplistic.
calculations, analysis, errors and comprehensive. For the essays, are missing. For the essays, at
conclusion are comprehensive (in some points are developed well. least one point is well
some cases not all sections will be A conclusion paragraph brings developed. There is a lack of
required), show insight, organization, the essay to a close. development of ideas and the
clarity and understanding. For the conclusion is simplistic/
essays, (3) points are clearly confusing/ too general.
developed and a concluding paragraph
brings the essay to a logical close.
Chemistry The essay demonstrates a consistent The essay demonstrates a good The essay demonstrates some The essay demonstrates
(mark x 2) and advanced command of chemical command of chemical principles. command of chemical minimal, poorly
principles. The chemical principles The chemical principles principles. The chemistry connected command of
discussed relate clearly and logically discussed mostly relate to the discussed shows some chemical principals. The
to the essay topic demonstrating deep essay topic, demonstrating a good connection between chemistry chemistry discussed is
understanding and insight of understanding of chemistry subject matter and the topic of general and vague.
chemistry subject matter and/or how subject matter and/or how the essay.
chemistry applies beyond the chemistry applies beyond the
classroom. classroom.
Topic The discussion of the essay/lab topic is The discussion of the essay/lab The discussion of the essay/lab The discussion of the
synthesis comprehensive, with careful analysis topic is good, with attention to topic is fair, with minimal essay/lab is inadequate.
(mark x 1) of ideas included in the question. items queried in the question. attention to items queried in the
question.
Extension/ Unexpected, original and/or new There is an attempt to make new Any extensions relate poorly or No attempt to make new
Originality/ points are introduced in the essay/lab. connections but some are very unclear. There is little connections is evident
Depth These extensions are clearly explained misunderstandings are evident. original thought in the and the essay does not
(mark x 1) and relate well to the topic/lab. The The essay/lab demonstrates a essay/lab. The essay/lab demonstrate a depth of
essay/lab demonstrates a deep good understanding of the topic. demonstrates some knowledge.
understanding of the topic. understanding of the topic.

Total /20
THE CANADIAN CHEMISTRY CONTEST 2017
PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)
All contestants should attempt this part of the contest before proceeding to Part B and/or Part C
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

1) Which of the following metals should be labelled with the WHMIS symbol 6) Given the following heats of formation, what is the enthalpy of combustion
for flammable substances ? for toluene shown in the following equation?

A) Al B) Ni C) Mg D) Pb E) Hg C7H8 (l) + 9 O2 (g)  7 CO2 (g) + 4 H2O (l)

2) A reaction AB + C, undergoes a single displacement reaction. Which of the Substance Hf (kJ mol–1) Substance Hf (kJ mol–1)
following would be a product of the reaction if A is a group 2 metal and C C7H8 (l) +12.0 H2O (l) -286
is a group 1 metal? CO2 (g) -394 O2 (g) 0
A) CA2 B) B C) CB D) A2 E) C2B A) 680 kJ mol–1 B) 692 kJ mol–1 C) –692 kJ mol–1
D) –3890 kJ mol–1 E) –3914 kJ mol–1
3) In which of the following situations could hydrogen bonding occur
between H2O and the solute? 7) Artificial photosynthesis involves splitting water with solar energy. This
A) ammonia gas dissolved in water clean energy reaction is: 2 H2O (l)  2 H2 (g) + O2 (g)
B) hydrogen gas dissolved in water
C) carbon dioxide gas in water Which of the following statements about the splitting of water is incorrect:
D) methane gas dissolved in water
E) hydrogen sulfide gas dissolved in water A) The oxidation state of hydrogen in water is +1
B) The oxidation state of hydrogen gas is 0
4) The exothermic thermite reaction between iron (III) oxide and aluminum C) Water is the oxidizing and reducing agent
metal occurs as follows: D) The oxidation state of oxygen in water is – 1
E) The oxygen atoms are oxidized in this process
Fe2O3 (s) + 2Al (s)  2Fe (s) + Al2O3 (s)
8) Cows are one of the most significant sources of methane (CH4) emitted
If 8.0 g of iron (III) oxide is combined with 5.4 g of aluminum metal, what into the atmosphere. The average cow produces 259 grams of methane
mass of iron metal will be produced? per day. The lower explosive limit (LEL) is the lowest concentration at
which there is a risk of an explosion. For methane, the LEL at SATP is 5.0%
A) 2.8 g B) 5.6 g C) 8.0 g D) 11 g E) 14 g v/v. Assuming a constant rate of methane emission from cows, how long
would it be safe to keep an average cow in a 10.0 m3 enclosed space at
5) Which of the following molecules has a molecular dipole? 25C and 100 kPa before there is a risk of explosion? The molar volume of
a gas at SATP is 24.8 L.
A) XeF4 B) SeF4 C) CF4 D) SiF4 E) KrF2
A) 30 hours B) 60 hours C) 90 hours D) 600 hours E) 900 hours
CCC 2017 page 2 of 4

9) Predict the conditions maximizing the rate of hydrogen gas production in 13) What is the correct relationship between the following two organic
the steam methane reforming reaction: substances?

CH4 (g) + H2O (g) ⇌ CO(g) + 3H2 (g) ∆H = +206 kJ mol-1

A) Low temperature, high pressure and a catalyst

B) Low temperature, low pressure and a catalyst A) non-superimposable mirror images
C) Low temperature, high pressure and no catalyst B) identical
D) High temperature, high pressure and a catalyst C) Structural, non-geometric isomers
E) High temperature, low pressure and a catalyst D) hydrocarbons with different molecular formulae
E) geometric isomers
10) The molality (m) of a solution is defined as the number of moles of solute
per kilogram of solvent. Lauryl alcohol (C12H26O) is prepared from coconut 14) Canada is a world-leader in the production of radionuclides such as
oil and is used to make sodium lauryl sulfate, a synthetic detergent. What is technetium-99m (99mTc), which is used to diagnose bone diseases. 99mTc
the molality of a solution of 17.1 g lauryl alcohol dissolved in 3.21 moles of has a relative atomic mass of 98.91 amu and exhibits first-order
ethanol (C2H6O)? radioactive decay with a half-life of 6.00 hours. If 8.62x10-12 mol of sodium
pertechnetate (Na99mTcO4) is injected into a 75 kg adult patient, what
A) 0.310 m B) 0.621 m C) 0.842 m D) 1.41 m E) 2.52 m mass of 99mTc would remain after 24 hours?

11) The following data were taken for the addition of solid barium fluoride to A) 1.46x10-9 g B) 2.13x10-10 g C) 3.66x10-11 g
enough water to make 100.0 mL of solution. What is the Ksp of barium D) 5.33x10-11 g E) 9.15x10-11 g
fluoride:
BaF2 (s) ⇌ Ba2+(aq) + 2 F–(aq)? 15) The first electron affinity (EA) for any element X is represented by the
equation: X (g) + e–  X– (g) + EA1. Negative values for electron affinity
Mass of solid Mass of solid Mass of solid indicate that energy is released when an atom gains an electron. Most
added (g) dissolved (g) undissolved (g) highschool textbooks teach the trend that electron affinity increases
across a period. According to the table below, which of the following
0.100 0.100 0
statement(s) is/are true?
0.200 0.200 0
0.300 0.300 0
Element Li Be B C N O F Ne
0.400 0.319 0.081
EA (kJ mol–1) –59.6 0 –26.7 –153.9 –7 –141 –328 0
A) 1.30 x 10–1 B) 3.25 x 10–2 C) 2.41 x 10-5
D) 6.03 x 10–6 E) 6.03 x 10–9
I. The absolute value of the energy released when an atom gains an
electron is always lower for metals than non-metals
12) The electron configuration 1s22s22p63s23p64s23d8 corresponds to which
II. Metals cannot form anions
of the following?
III. Neutral atoms with complete subshells do not release energy
during anion formation
A) Ni B) Ni2+ C) Fe D) Fe2+ E) Zn2+
A) I only B) II only C) III only
D) I and II only E) I and III only
CCC 2017 page 3 of 4

16) When aqueous magnesium chloride is added to a solution of silver nitrate, 18) A closed 600.0 mL flask contains solid mercuric oxide and air initially at
silver chloride is precipitated according to the following unbalanced 21.0C and 101.3 kPa. When heated, mercuric oxide decomposes
chemical equation: completely according to the reaction:

AgNO3 (aq) + MgCl2 (aq)  AgCl (s) + Mg(NO3)2 (aq) 2 HgO (s)  2 Hg (s) + O2 (g)
If excess magnesium chloride is added to the silver nitrate solution, which
After heating, the flask is at a temperature of 75.2C and has a
of the following diagrams best depicts the balanced chemical reaction after
it has gone to completion? pressure of 205.5 kPa. What mass of mercury metal is in the flask
when the reaction is complete?

A) 7.11 g B) 4.33 g C) 3.56 g D) 17.1 g E) 8.66 g

19) When you do extreme exercise, your body converts glucose to lactic acid
(HCH3H5O3). Lactic acid has a Ka= 1.38 x 10-4. Buffer systems maintain the
pH of your blood at 7.4 during exercise. Without buffers, what would your
blood pH range be at equilibrium if 4.00 x 10-3 mol L-1 of lactic acid
dissociated according to the equation:

HCH3H5O3 (aq) + H2O(l) ⇌ CH3H5O3–(aq) + H3O+(aq)

A) 2<pH<3 B) 3<pH<4 C) 4<pH<5 D) 5<pH<6 E) 6<pH<7

17) The process mass intensity (PMI) allows chemists to calculate how much
material is used when generating a target amount of product in a chemical 20) Molecular hydrogen is an essential feedstock for the industrial production
reaction. PMI is expressed as follows: of ammonia. Due to the impracticality of transporting molecular hydrogen,
it is produced at the site of ammonia production through steam methane
PMI = [(mass of all input materials) / (mass of desired product)] reforming, as follows:

To synthesize moclobemide, an anti-depressant pharmaceutical, H2O (g) + CH4 (g) ⇌ CO (g) + 3 H2 (g)
0.00381 moles of 4-(2-aminoethyl)morpholine (C6H14N2O) is dissolved in
20.0 mL of triethylamine (density: 0.726 g mL–1) and 0.00384 moles of Given a starting steam (H2O) to methane (CH4) mole ratio of 2.5:1.0, an
4-chlorobenzoyl chloride (C7H4Cl2O) is added. After rapid stirring for initial pressure of 28 atm, no starting carbon monoxide or molecular
30 minutes, 10.0 mL (density: 1.00 g mL–1) of water is added followed by hydrogen, determine the Kp if 62.5% of the initial methane is converted to
10.0 mL of dichloromethane (density: 1.325 g mL–1) and then the mixture products. Assume ideal gas behaviour.
transferred to a separatory funnel. After extraction, the dichloromethane is
dried with 5.0 g of magnesium sulfate. At the end of the process, 0.826 g of A) 1.7 x 100 B) 1.4 x 101 C) 2.1 x 102
pure moclobemide is recovered. D) 3.8 x 102 E) 5.6 x 103

The PMI for this reaction is:

A) 43.8 B) 47.1 C) 49.3 D) 53.2 E) 55.9

CCC 2017 page 4 of 4

21) If the rate law for an equation A + B + C  ABC is 24) Dopamine is a neurotransmitter found in the human brain that is involved
Rate= k [A]0[B][C]2 and the reactant concentration of all of the reactants in motor control. The IUPAC name for dopamine is 4-(2-
doubles, by what factor does the rate of reaction increase? aminoethyl)benzene-1,2-diol. Which of the following structures represents
a molecule of dopamine?
A) 3 B) 4 C) 6 D) 8 E) 10
HO
HO
22) When solid tin is added to a solution of silver nitrate, a single A) B) C)
displacement reaction occurs to generate silver metal. HO NH2
HO
HO NH2
If 1.2 g of tin is added to 50 mL of 0.20 M silver nitrate solution, which of NH2 OH
the following diagrams best describes the reaction once it has gone to
completion? HO HO
D) E)
NH2
HO HO NH2

25) Given the following half reactions and galvanic cell diagram
K+ (aq) + e–  K (s) E = –2.93 V
Cu2+ (aq) + 2e–  Cu (s) E = +0.34 V
Cr3+ (aq) + 3e–  Cr (s) E = –0.74 V

what is the theoretical potential of the cell?

A) 0.40 V B) 1.08 V
C) 1.85 V D) 2.19 V
E) 2.50 V

23) Hypophosphatemia is a condition of abnormally low phosphate

concentration in the human blood stream, occurring in 2% of hospitalized
patients. The treatment includes administration of intravenous phosphate
buffer to increase blood phosphate concentration. However, since
phosphoric acid is a weak acid, care needs to be taken to maintain blood
pH at 7.4. Given the data below, and assuming similar concentrations of
both species of the acid-base conjugate pair, determine the most effective
buffer combination to achieve a pH of 7.4.

H3PO4–; Ka = 7.2 x 10-3 H2PO4–; Ka = 6.3 x 10-8 HPO42–; Ka = 4.2 x 10-13

End of Part A of the contest
A) H3PO4 and H2PO4– B) H3PO4 and HPO42– C) H2PO4– and HPO42–
Go back and check your work
D) H2PO4– and PO43– E) HPO42– and PO4
THE 2017 CANADIAN CHEMISTRY CONTEST
for High School and CEGEP Students
PART B – EXTENDED RESPONSE SECTION (90 minutes)

Student will answer TWO questions as follows: all students must answer the experimental design question 1; students
have the choice between answering either question 2 or question 3. For each question, students should write a
scientific essay including appropriate equations, formulae and diagrams. Each essay is of equal value. Allocate
approximately equal time to each question. Scorers consider the accuracy and quality of the information and
presentation of the responses. A clear, concise, well-organized piece of written work will be rated more highly than a
long rambling one. A scientific calculator is allowed. No phones or communication devices are allowed.

1) Experimental Design: Gravimetric Analysis (mandatory question)

Through gravimetric analysis, researchers can determine the amount of one or more components present in a sample.
In this question, you will propose a procedure for determining the percent phosphorus in a sample of commercial
fertilizer. The main phosphorus containing component in the fertilizer sample is HPO42–. You can precipitate the
phosphorus spontaneously, without the addition of heat, according to the following equation:

5 H2O (l) + HPO42– (aq) + NH4+ (aq) + Mg2+ (aq) + OH- (aq)  MgNH4PO4 • 6H2O (s)

You have enough materials for one trial of your experiment. Write clear, step-by-step, detailed and easily -followed
procedure to determine the mass of phosphorus in your sample of fertilizer. You have 4.00 g of fertilizer, 0.025 moles
of 0.50 mol L–1 magnesium sulfate heptahydrate (MgSO4•7H2O) as your source of magnesium ions and 0.30 mol of 2.0
mol L–1 ammonium solution, 250 mL beakers, a stirring rod, an electronic balance, funnels, filter paper, a retort stand,
clamps, a wash bottle, distilled water, graduated cylinders, pipettes, burettes and safety goggles. Include diagrams of
equipment set up and the formulas you would use for calculations you propose. After providing your procedure, outline
at least two sources of error and how these errors might affect your results.

2) Thermodynamics
“…the deep impression that classical thermodynamics made upon me. It is the only physical theory of universal content
concerning which I am convinced that, within the framework of applicability of its basic concepts, it will never be
overthrown.” – Einstein (Klein, M., 1967)

What is the study of thermodynamics? What are the laws that govern thermodynamics? Do you think the study of
thermodynamics is important in high school chemistry? Why or why not? In your answer, be sure to clearly explain the
fundamental terms and concepts involved in thermodynamics and thermochemistry. Where possible use examples to
illustrate your ideas.

3) Chemistry and Innovation

New products hit the market everyday. Discuss an innovation based on chemistry that has garnered a lot of attention
in the past 15 years. Focus on explaining the chemistry involved in the innovation and discuss two or more of the
following: the innovation’s benefit to society, environmental impact, sustainability, longevity, effect on the market
economy and potential for further development.

References
Klein, M. J. (1967). Thermodynamics in Einstein's Thought. Science, 509-516. Retrieved from
http://www.rpgroup.caltech.edu/courses/aph105c/2006/articles/Klein_Einstein.pdf
THE CANADIAN CHEMISTRY CONTEST 2017
for high school and CEGEP students
(formerly the National High School Chemistry Examination)

PART C: CANADIAN CHEMISTRY OLYMPIAD

Final Selection Examination 2017
Free Response Development Problems (90 minutes)
This segment has five (5) questions. While students are expected to attempt all questions for a
complete examination in 1.5 hours, it is recognized that backgrounds will vary and students will
not be eliminated from further competition because they have missed parts of the paper.

— PLEASE READ — PART A ( )

Correct Answers
1. BE SURE TO COMPLETE THE INFORMATION REQUESTED AT THE
BOTTOM OF THIS PAGE BEFORE BEGINNING PART C OF THE
EXAMINATION. 25 x 1.6 = ......... /040

2. STUDENTS ARE EXPECTED TO ATTEMPT ALL QUESTIONS OF

4. .................... /012
4. ONLY NON-PROGRAMMABLE CALCULATORS MAY BE USED ON
THIS EXAMINATION. 5. .................... /012

5. NOTE THAT A PERIODIC TABLE AND A LIST OF SOME PHYSICAL

CONSTANTS WHICH MAY BE USEFUL CAN BE FOUND ON A DATA
SHEET PROVIDED AT THE END OF THIS EXAMINATION.
TOTAL ............ /100
Name _____________________________ School _____________________________
(LAST NAME, Given Name; Print Clearly)

City & Province ___________ Date of Birth

E-Mail ____________ Home Telephone ( ) - _

Years at a Canadian high school ___ No. of chemistry courses at a Québec CÉGEP ___
Male Canadian Citizen Landed Immigrant Visa Student 
Female Passport valid until February 2018 Nationality of Passport __________
Teacher __________________________ Teacher E-Mail ___________________________ 
GENERAL CHEMISTRY

1. Sulfur dioxide (SO2) is produced by volcanoes and in various industrial processes. Since coal
and petroleum often contain sulfur compounds, their combustion generates sulfur dioxide.
Further oxidation of SO2, usually in the presence of a catalyst such as NO2, forms H2SO4, and
thus acid rain. This is one of the causes for concern over the environmental impact of the use of
these fuels as power sources.

(a). Draw the best two resonance structures for sulfur dioxide, SO2, which do not involve sulfur
using its d-orbitals in "hypervalency". Be sure to include all formal charges (should they exist)
and lone pairs of electrons in your structures.

4 marks

(b). Draw the best resonance form for sulfur dioxide in which sulfur does use its d-orbitals in
bonding. Be sure to include all formal charges (should they exist) and lone pairs of electrons in
your structure.

2 marks

(c). What is the hybridization of the sulfur atom in SO2?

2 marks

(d). Write a reaction involving SO2 which illustrates how its sulfur atom may act as a Lewis base
in reaction with a Lewis acid. In your reaction, designate the Lewis acid as “A”.

2 marks
-2-
(e). Write a reaction involving SO2 which illustrates how its sulfur atom may serve as a Lewis
acid in reaction with a Lewis base. In your reaction, designate the Lewis base as “B”.

2 marks

-3-
PHYSICAL CHEMISTRY

2. Electrons moving back and forth in a one-dimensional box may only occupy discrete energy
levels given by the formula

h2 n = 1, 2, 3...
E = n2
2
8mL

in which n is the energy level, h is Planck’s constant, m is the mass of the electron, and L is the
length of the box.

(a). Calculate the energy of an electron in the second energy level of a box with length 1.00 nm.

1 mark

Pi electrons in a linear, conjugated molecule or section of a molecule can be modeled after the
one-dimensional box system.

(b). In the molecule 1,8-diphenyl-1,3,5,7-octatetratriene shown below, how many pi electrons are
part of the linear, conjugated system between the two phenyl groups?

number of pi electrons: ______

1 mark

(c). The linear, conjugated system in 1,8-diphenyl-1,3,5,7-octatetratriene can be modeled roughly

after a one-dimensional box. How many orbitals do the pi electrons in the system occupy when
the molecule is in the ground state?

1 mark

(d). The Highest Occupied Molecular Orbital, or “HOMO”, is the highest energy level orbital
that is occupied by electrons in ground state. Given a linear, conjugated system with N electrons,
what is the equation for the energy of the HOMO in terms of h, m, and L?

1 mark

-4-
(e). The Lowest Unoccupied Molecular Orbital, or “LUMO”, is the lowest energy level orbital
that is not occupied by electrons in ground state. Given a linear, conjugated system with N
electrons, what is the equation for the energy difference between the HOMO and LUMO in
terms of h, m, and L?

2 marks

Retinal is a form of Vitamin A produced by oxidative cleavage of carotenoids. Retinal has the
following structure:

(f). The conjugated system in retinal can be roughly modeled as a one-dimensional box. Given
that the average length of a C – C bond in the system is 0.140 nm and the average length of a
C =O double bond is 0.123 nm, estimate the length of the box.

2 marks
(g). Calculate the wavelength of light that retinal can absorb to reach an excited state.

4 marks
-5-
INORGANIC CHEMISTRY

3. Titanium is an economically important element used principally in the aerospace industry, but
also in medical prosthetics and as an industrial pigment. For example, the white lettering on
Skittles and M&M candies is made with titanium dioxide, which was recently declared a possible
carcinogen in humans by the International Agency for Research on Cancer (IARC).

(a). Among its minerals, titanium most commonly occurs with an oxidation number of +4. State
the complete electron configuration for titanium, corresponding to this oxidation number. Do not
use short-hand notation.

1 mark

(b). Ilmenite, FeTiO3, is one of the principal titanium-bearing minerals. An essential step in
producing high-purity titanium is the chloride process. Balance the chemical equation below for
the chloride process.

FeTiO3(s) + Cl2(g) + C(s, graphite)  TiCl4(l) + FeCl3(s) + CO(g)

1 mark

(c). Write a balanced chemical equation for the complete hydrolysis of titanium tetrachloride.

1 mark

Though titanium metal can be produced from ilmenite by the sulfate process, a higher yield can
be obtained by refining the less common mineral rutile. The rutile unit cell (based upon a
body-centred tetragonal arrangement of titanium atoms) is shown below. The oxygen atoms are
dark-coloured spheres in the rutile unit cell.

(d). Name the localized geometries around oxygen and titanium.

O: _ Ti: _

1 mark
-6-
(e). Given the dimensions of the unit cell, a = b = 0.4584 nm and c = 0.2953 nm, calculate the
density (in g cm-3) of the rutile form of titanium dioxide.

3 marks
(f). Titanium tetrachloride is a liquid at standard ambient temperature and pressure (SATP).
Given ∆Hvap of +37.5 kJ mol-1, a vapour pressure of 1.70 kPa at SATP and using the
Clausius-Clapeyron equation (below), calculate the boiling temperature of TiCl4. Assume no
change in external pressure.

2 marks
(g). High-purity titanium metal can be prepared industrially in a stainless-steel, high-pressure
reactor from titanium tetrachloride and magnesium metal, according to the Kroll process.
Assume the processing temperature is 900°C and a positive pressure (P > 100 kPa) is maintained
within the reactor by means of an inert gas. Using the data provided below, explain how titanium
metal could be produced by the Kroll process with the use of a diagram and a balanced chemical
reaction. If you were unable to obtain an answer from part (f), use 150°C for the boiling point of
TiCl4.
Substance Melting point (°C) Boiling point (°C) Density at 25°C (g cm-3)
TiCl4 -24 see part (f) 1.726
Mg 650 1091 1.584
Ti 1668 3287 4.506
MgCl2 714 1412 2.325

3 marks
-7-
ORGANIC CHEMISTRY
4. GlaxoWellcome first marketed the pharmaceutical bupropion (structure below) in 1985 under
the trade-name Wellbutrin® as a treatment for depression. Many smokers taking the drug
reported that after one or two weeks their craving for tobacco ceased and they were able to quit
smoking with few withdrawal symptoms. Bupropion therefore began to be marketed in 1997
with a new name (Zyban®) for use as an aid in smoking cessation.

+
N Cl- Bupropion
Cl H H

Bupropion can be prepared from benzene according to the following scheme:

Q T
S V
R C9H10O U
O
Cl

Br2, H+ catalyst
X
Z C4H11N
Bupropion Y W

(a). Draw the structures of reagents Q, R, T, U, X and Z.

Q= R= T=

U= X= Z=

3 marks
(b). Draw the structures of intermediate compounds S, W and Y.

S= W= Y=

3 marks
(c). State how many stereoisomers of bupropion exist.

0.5 marks
-8-
(d). State whether you would expect bupropion to be soluble or insoluble in water, explaining
your reasoning IN LESS THAN TEN WORDS.

0.5 marks

(e). Draw the major organic product formed when intermediate compound V reacts with each of
the following five sets of reagents:

NaBH4, ethanol:

(1) CH3MgBr, ether, then (2) H3O+:

H2, Pt metal:

CH3NH2, H+ catalyst:

(CH3)2NH, H+ catalyst:

5 marks

-9-
ANALYTICAL CHEMISTRY

5. The concentration of copper(II) ions in a dilute solution may be determined by a two-step

titration procedure as follows:

 the sample is treated with excess potassium iodide, resulting in the formation of copper(I)
iodide and iodine
 the iodine formed is titrated with sodium thiosulfate

(a). Balance the net ionic equation for the reaction of copper(II) with iodide.

_ Cu2+ (aq) + _ I– (aq)  _ CuI (s) + _ I2 (aq)

1 mark
(b). Balance the net ionic equation for the reaction of iodine with thiosulfate.

_ I2 (aq) + _ S2O32– (aq)  _ I– (aq) + _ S4O62– (aq)

1 mark

(c). Using these balanced equations, derive a relationship between the number of moles of
copper(II) nCu in the sample and the number of moles of thiosulfate nT required to reach the
stoichiometric equivalence point for the titration.

2 marks

(d). An excess of iodide is added to 50.00 mL of a solution containing copper(II). The solution
is then titrated with 0.1002 M thiosulfate, requiring 32.07 mL to reach the equivalence point.
Determine the initial concentration of copper(II) in the sample, making sure to show all steps in
your calculation.

2 marks
- 10 -
(e). It is very important that an excess of iodide is used in the first step of this procedure. What
does the excess iodide do?

2 marks

(f). Suggest a suitable indicator that you could use for this titration. At what point in the
procedure would you add this indicator?

2 marks

(g). Titrations involving iodine require a number of precautions. Suggest two possible issues,
and the precautions you would take to deal with them.

2 marks

--END OF PART C--

- 11 -
Data Sheet
Fiche de données
1 18
1 2
H He
1.008 2 13 14 15 16 17 4.003
Relative Atomic Masses (2012, IUPAC) Masses Atomiques Relatives (UICPA, 2012)
3 4 *For the radioactive elements the *Dans le cas des éléments radioactifs, la masse
5 6 7 8 9 10
Li Be atomic mass of an important isotope is given atomique fournie est celle d’un isotope important
B C N O F Ne
6.941 9.012 10.81 12.01 14.01 16.00 19.00 20.18
11 12 13 14 15 16 17 18
Na Mg Al Si P S Cl Ar
22.99 24.31 3 4 5 6 7 8 9 10 11 12 26.98 28.09 30.97 32.07 35.45 39.95
19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36
K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr
39.10 40.08 44.96 47.87 50.94 52.00 54.94 55.85 58.93 58.69 63.55 65.38 69.72 72.61 74.92 78.96 79.90 83.80
37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54
Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe
85.47 87.62 88.91 91.22 92.91 95.96 (98) 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3
55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86
Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn
132.9 137.3 138.9 178.5 180.9 183.9 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 (209) (210) (222)
87 88 89 104 105 106 107 108 109 110 111 112 113 114 115 116 117 118
Fr Ra Ac Rf Db Sg Bh Hs Mt Ds Rg Cn Uut Fl Uup Lv Uus Uuo
(223) (226) (227) (261) (262) (266) (264) (277) (268) (269) (272) (285) (284) (289) (288) (292) (294)

58 59 60 61 62 63 64 65 66 67 68 69 70 71
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
140.1 140.9 144.2 (145) 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.0 175.0

90 91 92 93 94 95 96 97 98 99 100 101 102 103

Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
232.0 (231.0 (238.0) (237) (244) (243) (247) (247) (251) (252) (257) (258) (259) (262)

Symbol Value
Symbole Quantité numérique

Atomic mass unit amu 1.66054 x 10-27 kg Unité de masse atomique

Avogadro’s number N 6.02214 x 1023 mol-1 Nombre d’Avogadro
Charge of an electron e 1.60218 x 10-19 C Charge d’un électron
Dissociation constant (H2O) Kw 1.00 x 10-14 (25ºC) Constante de dissociation de l’eau (H2O)
Faraday’s constant F 96 485 C mol-1 Constante de Faraday
Gas constant R 8.31451 J K-1 mol-1 Constante des gaz
0.08206 L atm K-1 mol-1
Mass of an electron me 9.10939 x 10-31 kg Masse d’un électron
Mass of a neutron mn 1.67493 x 10-27 kg Masse d’un neutron
Mass of a proton mp 1.67262 x 10-27 kg Masse d’un proton
Planck’s constant h 6.62608 x 10-34 J s Constante de Planck
Speed of light c 2.997925 x 108 m s-1 Vitesse de la lumière
Rydberg constant R∞ 1.097 x 107 m-1 Constante de Rydberg

1Å = 1 x 10-10 m STP/TPN SATP/TPAN

1 atm = 101.325 kPa 273.15 K 298 K
1 bar = 1 x 105 Pa 100 kPa 100 kPa
THE CANADIAN CHEMISTRY CONTEST 2017
PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)
All contestants should attempt this part of the contest before proceeding to Part B and/or Part C
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

A) Al B) Ni C) Mg D) Pb E) Hg C7H8 (l) + 9 O2 (g)  7 CO2 (g) + 4 H2O (l)

Fe2O3 (s) + 2Al (s)  2Fe (s) + Al2O3 (s) 8) Cows are one of the most significant sources of methane (CH4) emitted
into the atmosphere. The average cow produces 259 grams of methane
If 8.0 g of iron (III) oxide is combined with 5.4 g of aluminum metal, what per day. The lower explosive limit (LEL) is the lowest concentration at
mass of iron metal will be produced? which there is a risk of an explosion. For methane, the LEL at SATP is 5.0%
v/v. Assuming a constant rate of methane emission from cows, how long
A) 2.8 g B) 5.6 g C) 8.0 g D) 11 g E) 14 g would it be safe to keep an average cow in a 10.0 m3 enclosed space at
25C and 100 kPa before there is a risk of explosion? The molar volume of
5) Which of the following molecules has a molecular dipole? a gas at SATP is 24.8 L.

A) XeF4 B) SeF4 C) CF4 D) SiF4 E) KrF2 A) 30 hours B) 60 hours C) 90 hours D) 600 hours E) 900 hours
CCC 2017 page 2 of 4

9) Predict the conditions maximizing the rate of hydrogen gas production in 13) What is the correct relationship between the following two organic
the steam methane reforming reaction: substances?

CH4 (g) + H2O (g) ⇌ CO(g) + 3H2 (g) ∆H = +206 kJ mol-1

A) Low temperature, high pressure and a catalyst A) non-superimposable mirror images

B) Low temperature, low pressure and a catalyst B) identical
C) Low temperature, high pressure and no catalyst C) Structural, non-geometric isomers
D) High temperature, high pressure and a catalyst D) hydrocarbons with different molecular formulae
E) High temperature, low pressure and a catalyst E) geometric isomers

10) The molality (m) of a solution is defined as the number of moles of solute 14) Canada is a world-leader in the production of radionuclides such as
per kilogram of solvent. Lauryl alcohol (C12H26O) is prepared from coconut technetium-99m (99mTc), which is used to diagnose bone diseases. 99mTc
oil and is used to make sodium lauryl sulfate, a synthetic detergent. What is has a relative atomic mass of 98.91 amu and exhibits first-order
the molality of a solution of 17.1 g lauryl alcohol dissolved in 3.21 moles of radioactive decay with a half-life of 6.00 hours. If 8.62x10-12 mol of sodium
ethanol (C2H6O)? pertechnetate (Na99mTcO4) is injected into a 75 kg adult patient, what
mass of 99mTc would remain after 24 hours?
A) 0.310 m B) 0.621 m C) 0.842 m D) 1.41 m E) 2.52 m
A) 1.46x10-9 g B) 2.13x10-10 g C) 3.66x10-11 g
11) The following data were taken for the addition of solid barium fluoride to D) 5.33x10-11 g E) 9.15x10-11 g
enough water to make 100.0 mL of solution. What is the Ksp of barium
fluoride: 15) The first electron affinity (EA) for any element X is represented by the
BaF2 (s) ⇌ Ba2+(aq) + 2 F–(aq)? equation: X (g) + e–  X– (g) + EA1. Negative values for electron affinity
indicate that energy is released when an atom gains an electron. Most
Mass of solid Mass of solid Mass of solid highschool textbooks teach the trend that electron affinity increases
added (g) dissolved (g) undissolved (g) across a period. According to the table below, which of the following
statement(s) is/are true?
0.100 0.100 0
0.200 0.200 0
Element Li Be B C N O F Ne
0.300 0.300 0
EA (kJ mol–1) –59.6 0 –26.7 –153.9 –7 –141 –328 0
0.400 0.319 0.081

A) 1.30 x 10–1 B) 3.25 x 10–2 C) 2.41 x 10-5

I. The absolute value of the energy released when an atom gains an
D) 6.03 x 10–6 E) 6.03 x 10–9
electron is always lower for metals than non-metals
II. Metals cannot form anions
12) The electron configuration 1s22s22p63s23p64s23d8 corresponds to which
III. Neutral atoms with complete subshells do not release energy
of the following?
during anion formation
A) Ni B) Ni2+ C) Fe D) Fe2+ E) Zn2+
A) I only B) II only C) III only
D) I and II only E) I and III only
CCC 2017 page 3 of 4

A) 7.11 g B) 4.33 g C) 3.56 g D) 17.1 g E) 8.66 g

HCH3H5O3 (aq) + H2O(l) ⇌ CH3H5O3–(aq) + H3O+(aq)

A) 2<pH<3 B) 3<pH<4 C) 4<pH<5 D) 5<pH<6 E) 6<pH<7

The PMI for this reaction is:

A) 43.8 B) 47.1 C) 49.3 D) 53.2 E) 55.9

CCC 2017 page 4 of 4

25) Given the following half reactions and galvanic cell diagram
K+ (aq) + e–  K (s) E = –2.93 V
Cu2+ (aq) + 2e–  Cu (s) E = +0.34 V
Cr3+ (aq) + 3e–  Cr (s) E = –0.74 V

what is the theoretical potential of the cell?

A) 0.40 V B) 1.08 V
C) 1.85 V D) 2.19 V
E) 2.50 V

23) Hypophosphatemia is a condition of abnormally low phosphate

H3PO4–; Ka = 7.2 x 10-3 H2PO4–; Ka = 6.3 x 10-8 HPO42–; Ka = 4.2 x 10-13

End of Part A of the contest
A) H3PO4 and H2PO4– B) H3PO4 and HPO42– C) H2PO4– and HPO42–
Go back and check your work
D) H2PO4– and PO43– E) HPO42– and PO4
Rubric guideline for evaluating the CCC (Part B) essay topics (out of 20 marks)
Criteria 4 marks 3 marks 2 marks 1 mark
Format The essay is written with an engaging, The essay has an interesting, The introduction is partially The essay is disorganized
(mark x 1) clear introduction. For the lab design clear introduction. The lab developed. The lab format is and/or confusing and
the purpose, materials, procedure, format is evident but not evident but some of the sections simplistic.
calculations, analysis, errors and comprehensive. For the essays, are missing. For the essays, at
conclusion are comprehensive (in some points are developed well. least one point is well
some cases not all sections will be A conclusion paragraph brings developed. There is a lack of
required), show insight, organization, the essay to a close. development of ideas and the
clarity and understanding. For the conclusion is simplistic/
essays, (3) points are clearly confusing/ too general.
developed and a concluding paragraph
brings the essay to a logical close.
Chemistry The essay demonstrates a consistent The essay demonstrates a good The essay demonstrates some The essay demonstrates
(mark x 2) and advanced command of chemical command of chemical principles. command of chemical minimal, poorly
principles. The chemical principles The chemical principles principles. The chemistry connected command of
discussed relate clearly and logically discussed mostly relate to the discussed shows some chemical principals. The
to the essay topic demonstrating deep essay topic, demonstrating a good connection between chemistry chemistry discussed is
understanding and insight of understanding of chemistry subject matter and the topic of general and vague.
chemistry subject matter and/or how subject matter and/or how the essay.
chemistry applies beyond the chemistry applies beyond the
classroom. classroom.
Topic The discussion of the essay/lab topic is The discussion of the essay/lab The discussion of the essay/lab The discussion of the
synthesis comprehensive, with careful analysis topic is good, with attention to topic is fair, with minimal essay/lab is inadequate.
(mark x 1) of ideas included in the question. items queried in the question. attention to items queried in the
question.
Extension/ Unexpected, original and/or new There is an attempt to make new Any extensions relate poorly or No attempt to make new
Originality/ points are introduced in the essay/lab. connections but some are very unclear. There is little connections is evident
Depth These extensions are clearly explained misunderstandings are evident. original thought in the and the essay does not
(mark x 1) and relate well to the topic/lab. The The essay/lab demonstrates a essay/lab. The essay/lab demonstrate a depth of
essay/lab demonstrates a deep good understanding of the topic. demonstrates some knowledge.
understanding of the topic. understanding of the topic.

Total /20
THE CANADIAN CHEMISTRY CONTEST 2016
PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)
All contestants should attempt this part of the contest before proceeding to Part B and/or Part C
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

1) WHMIS 2015 is the updated labelling system which conforms to the 5) After a chemist stirs the contents of a beaker, the rate of a reaction
new international standard of classifying hazardous materials. Although all between reactants A and B increases by a factor of four. Use the diagrams
of the compounds below would require some labelling for other below to help you to determine the main reason why the rate of reaction
characteristics, which compound would NOT require the oxidizer increases.
label shown to the right?

A) potassium permanganate B) sodium chlorate

C) ethanol D) nitric acid
E) hydrogen peroxide
A) Reaction surface area increases B) Activation energy increases
2) A 0.48 g piece of magnesium metal is placed in hydrochloric acid. C) Reactant concentrations increase D) Total kinetic energy increases
Assuming the hydrochloric acid is in excess and the magnesium reacts E) Average kinetic energy increases
completely, how many grams of hydrogen gas are produced?
6) The limit for lead in drinking water is 0.015 ppm according to the
A) 0.010 g B) 0.040 g C) 0.080 g Environmental Protection Agency (EPA). A 100.0 mL sample of well water
D) 0.48 g E) 0.96 g
tested for dissolved Pb2+ with a saturated potassium iodide solution
3) If the total pressure increases in each of the reaction mixtures below, for produced 1.7 mg of yellow lead iodide precipitate. How many times higher
which reaction would the product yield remain unchanged at equilibrium? than the EPA limit was the concentration of lead in the well water?

A) 110 times B) 1100 times C) 510 times D) 700 times E) 51 times

A) CO (g) + H2O (g) ⇋ CO2 (g) + H2 (g)
B) 2 NO (g) + Cl2 (g) ⇋ 2 NOCl (g) 7) A common method for cleaning up an acid spill is to spread sodium
C) 2 H2S (g) ⇋ 2 H2 (g) + S2 (g) carbonate over the spill to neutralize it. If 50.0 mL of 0.75 mol L–1HCl
spilled on the countertop, what is the minimum amount of sodium
D) 2 H2 (g) + O2 (g) ⇌ 2 H2O (g)
carbonate required to neutralize the spill?
E) 3 H2 (g) + CO (g) ⇌ CH4 (g) + H2O (g)
A) 1.6 g B) 1.9 g C) 2.0 g D) 3.1 g E) 4.0 g
4) Which of the following compounds has the smallest bond angle?
8) Which element would have its highest energy valence electron correspond to
A) BF3 B) CF4 C) NF3 D) OF2 E) ClF3 the following quantum numbers? n= 4, l = 2

A) Sc B) Y C) K D) Zn E) Ga
CCC 2016 page 2 of 4

9) The 1st and 3rd ionization energies of aluminum are 577.5 kJ mol–1 and 13) A student performs the following reaction to make solid sulfur:
2744.8 kJ mol–1 respectively. What data best matches the 2nd and 4th
ionization energies of aluminum? Na2S2O3 (aq) + 2 HCl (aq)  2 NaCl (aq) + S (s) + SO2 (g) + H2O (l)

2nd ionization energy 4th ionization energy The student records the following data at the start of the reaction:
Concentration (mol L–1) Volume (mL)
(kJ mol–1) (kJ mol–1)
Na2S2O3 (aq) 0.45 130
A) 700 3500
HCl (aq) 0.15 400
B) 700 5000
C) 700 11000 If the student recovers 0.89 g of solid sulfur from the experiment, what is
D) 1800 11000 the % yield of the reaction?
E) 1800 5000
A) 46% B) 48% C) 75% D) 89% E) 93%
10) Levobunolol (structure below) is used topically to treat glaucoma, an
eye disorder which causes damage to the optic nerve. 14) A student places 0.750 g of solid sodium hydroxide (NaOH) into
20.00 mL of water at 25.0 C inside a coffee cup calorimeter. The final
temperature of the calorimeter contents is 34.6 C. The density of water is
O OH 1.0 g mL–1. Assume the specific heat capacity of the solution approximates
O levobunolol
that of water at 4.184 J g –1 C–1 and the calorimeter has 100% efficiency.
N What is the ΔHrxn for the dissolution reaction below?
H NaOH (s)  NaOH (aq)
Which of the following functional groups are contained within the structure
of levobunolol? A) –42.8 kJ mol–1 B) – 44.4 kJ mol–1 C) – 803 J mol–1
D) –833 J mol–1 E) – 1070 J mol–1
A) amine, ketone, ether, phenol B) amide, ketone, ether, alcohol
C) amine, ketone, ester, alcohol D) amine, ketone, ether, alcohol 15) Canadian cities began adding fluoride to their drinking water in the
E) amine, aldehyde, ether, alcohol mid-1950s, as a means to reducing dental caries (cavities) in children.
Sodium fluorosilicate (Na2SiF6), a by-product of the industrial processing
11) Penicillamine is an important organic compound used in the treatment of phosphate minerals, can be added to drinking water to produce free
of rheumatoid arthritis. One molecule of penicillamine contains a single fluoride ions. A drinking water analysis for a Canadian city revealed the
sulfur atom and the weight percentage of sulfur in penicillamine is 21.49%. following data:
What is the molecular weight of penicillamine in g mol–1? pH = 7.60 [F–] = 3.2 x 10–5 mol L–1
A) 85.40 B) 101.3 C) 125.2 D) 137.6 E) 149.2
Given that the pKa of hydrofluoric acid (HF) is 3.17, determine the
concentration of HF in the drinking water of this Canadian city. Assume a
12) For a spontaneous reaction, which relationship below is always true?
water temperature of 25°C.

A) ΔG⁰ rxn > 0 B)  S universe > 0 C)  S universe < 0

A) 5.4 x 10–2 mol L–1 B) 3.2 x 10–5 mol L–1 C) 6.4 x 10–5 mol L–1
D) ΔH⁰ rxn > 0 E) ΔH⁰ rxn < 0
D) 1.9 x 10–8 mol L–1 E) 1.2 x 10–9 mol L–1
CCC 2016 page 3 of 4

16) The transition metal rhenium (Re), is among the rarest elements in the 18) Solid lead carbonate precipitate can be formed from mixing aqueous
earth’s crust. The precursor to the pure metal, ammonium perrhenate, is lead nitrate and sodium carbonate:
produced during the refinement of molybdenum ores. The principal
application of rhenium is as an alloy with nickel, used in jet engine Pb(NO3)2 (aq) + Na2CO3 (aq)  PbCO3(s) + 2 NaNO3 (aq)
components. Consider the unbalanced chemical equation for the hydrogen
reduction of ammonium perrhenate: If 360 mL of 0.15 mol L–1 sodium carbonate was
combined with 45 mL of 0.60 mol L–1 lead nitrate,
__ NH4ReO4 + __ H2 __ Re + __H2O + __ NH3
which of the following diagrams best describes the
system once it has gone to completion?
Assume the oxidation number of nitrogen in the reactants and products is
unchanged. Determine the sum of the smallest integer coefficients for the
stoichiometrically balanced chemical equation.

A) 5 B) 14 C) 18 D) 20 E) 21

17) The metric known as reaction mass efficiency (RME) provides a way to
assess how much reactant material ends up in a desired product at the end
of a chemical reaction. One way of expressing RME is as follows:

mass of desired product

reaction mass efficiency =
(total input mass−mass of recycled material)

0.115 moles of cholesterol (C27H46O) was reacted with 0.365 moles of 19) Naphthalene is a white crystalline solid, traditionally used as the
molecular bromine to form 0.102 moles of dibromocholesterol in an primary ingredient in mothballs. It has the chemical
addition reaction (shown below). It was possible to recover and recycle formula C10H8, and its structure is shown to the right.
0.151 moles of molecular bromine from the reaction mixture. Rank the solubility of naphthalene in the following
solvents from most to least soluble.

I. water II. hexane III. ethanol IV. hexanol

cholesterol A) II > IV > III > I B) IV > II > III > I C) I > III > II > IV
Br2 D) II > III > IV > I E) IV > III > II > I
H H
20) Vitamin-B3, or Niacin, is an essential nutrient for humans. Its
H H H H molecular structure is shown on the right. A 0.0050 mol L–1
HO HO
Br solution of Niacin in water has a pH of 3.56. What is the
Br percentage ionization of niacin in water?

What is the percentage reaction mass efficiency for this process? A) 1.4 % B) 2.8 % C) 3.6 % D) 5.5 % E) 7.8%

A) 43.3 % B) 54.3% C) 70.9% D) 84.6 % E) 89.1%

CCC 2016 page 4 of 4

21) 2- propanol reacts with oxygen as follows: 23) A gaseous anesthetic with an unknown molecular formula is 85.63%
carbon and 14.37% hydrogen by mass. What is the molecular formula of
2 C3H7OH (l) + 9 O2 (g)  6 CO2 (g) + 8 H2O (g) the unknown if 0.45 L of the compound combusts with excess oxygen at
If 0.500 moles of 2-propanol react in the presence of 4.00 moles of oxygen, 120.0C at 72.93 kPa to form 2.70 L of an equimolar mixture of carbon
how many kilojoules of heat would be absorbed or released? A table of dioxide and water vapour?
average bond energies is given below.
A) C3H6 B) C4H8 C) C5H10 D) C6H12 E) C7H14
Bond Type Bond Energy Bond Type Bond Energy
(kJ mol–1) (kJ mol–1) 24) Given the following data table for the reaction 2 A + B2 → 2 AB
C-H 413 O=O 495
O-H 467 C=O 799 [A] mol L–1 [B2] mol L–1 Rate of Reaction (mol L–1 s–1)
C-O 358 C-C 347 0.100 0.100 0.117
0.200 0.100 0.468
A) – 1890 kJ B) + 1890 kJ C) – 1680 kJ 0.200 0.200 0.936
D) – 946 kJ E) + 473 kJ
What is the rate of reaction in mol L–1 s–1 if [A] = [B2] = 0.300 mol L–1?
22) For the cell depicted, the half-reactions are:
A) 1.87 B) 2.81 C) 3.02 D) 3.16 E) 3.51
Zn2+ (aq) + 2e– → Zn(s) E° = –0.76 V
Cu2+ (aq) + 2e– → Cu(s) E° = +0.34 V
25) Flask 1 Flask 2
Which of the following is true for the spontaneous cell reaction? 2.0 g of H2 16.0 g of O2
gas at 25C gas at 25C
A) Zn is the anode; the electron flow is from anode to cathode; anions
and P1 and P2
migrate through the salt bridge from the Zn/Zn2+ to the Cu/Cu2+
half-cell and cations migrate in the opposite direction. Both Flask 1 and Flask 2 have a volume of exactly 2.0 L, KE is the average
B) Zn is the cathode; the electron flow is from anode to cathode; kinetic energy, and P is pressure. Which statement below is TRUE?
anions migrate through the salt bridge from the Zn/Zn2+ to the
Cu/Cu2+ half-cell and cations migrate in the opposite direction.
A) P1 = P2
C) Zn is the anode; the electron flow is from cathode to anode; anions
B) the KE of the particles in flask 1 < the KE of the particles in flask 2
migrate through the salt bridge from the Zn/Zn2+ to the Cu/Cu2+
half-cell and cations migrate in the opposite direction. C) the number of particles in flask 1 > the number of particles in flask 2
D) Zn is the cathode; the electron flow is from anode to cathode; D) the number of collisions in flask 1 = number of collisions in flask 2
cations migrate through the salt bridge from the Zn/Zn2+ to the E) 2 P1 = P2
Cu/Cu2+ half-cell and anions migrate in the opposite direction.
E) Zn is the anode; the electron flow is from anode to cathode;
cations migrate through the salt bridge from the Zn/Zn2+ to the
End of Part A of the contest
Cu/Cu2+ half-cell and anions migrate in the opposite direction.
Go back and check your work
THE 2016 CANADIAN CHEMISTRY CONTEST
for High School and CEGEP Students

PART B – EXTENDED RESPONSE SECTION (90 minutes)

In this section, respond to TWO questions. For each question, write a scientific essay including
appropriate equations, formulae and diagrams. Each essay is of equal value. The quality of both
responses is considered in the final competition. Allocate approximately equal time to each question.
The judging is based on the accuracy of the information and presentation of the responses. A clear,
concise, well-organized piece of written work will be rated more highly than a long rambling one. A
scientific calculator is allowed. No phones or any communication devices are allowed.

1) Experiment Design: Identifying an Unknown Solution

You must identify the contents of a 500 mL bottle of an unknown clear solution found in the
acid/base chemical storage area in your high school. Universal indicator paper qualitatively
indicates the solution has a pH of 3.
Write a procedure outlining how you would experimentally determine the identity and
concentration of the unknown solution. You may use any equipment, reagents, and materials
typically found in a high school chemistry classroom. Clearly present your experimental steps and
the reasoning behind them. You must demonstrate a thorough understanding of the experiment
you are performing, the data you need to collect, and the data analysis you must perform.
Apply all of the necessary precautions normally used while handling any acid or base. Your
high school only has hydrochloric acid, acetic acid (CH3COOH, Ka = 1.8 x 10–5), lactic acid (HC3H5O3,
Ka = 1.38 x 10–4), monochloroacetic acid (HC2H2ClO2, Ka = 1.35 x 10–3), sodium hydroxide, and
ammonia (NH3, Kb = 1.8 x 10–5) in stock, and your unknown solution must be one of these.

2) Catalytic Chemistry

Catalysts are everywhere. In our bodies, enzymes catalyze all sorts of reactions. New
photocatalytic processes split water into hydrogen and oxygen and many industrial processes
depend on catalysts. Catalysis is essential not only in research but also for the global economy and
for technological advancement. Many commercial chemical products require one or more catalytic
steps in their syntheses and approximately one fifth of Nobel Prizes awarded in Chemistry have
been for applications of catalysis.
Discuss the use of catalysis in at least two different fields, including but not limited to
biochemistry, organic chemistry, inorganic chemistry, and materials chemistry. In your essay, be
sure to explain how catalysts work and why they are useful, and provide specific examples to
support your discussion.
3) The Future of the Periodic Table

On December 30th, 2015, IUPAC ratified the existence of four new elements, giving credit for
element 113 to Japanese researchers at the RIKEN institute in Wako, Japan, and elements 115, 117
and 118 to the collaboration among the Joint Institute for Nuclear Research in Dubna, Russia, the
Lawrence Livermore National Laboratory in California, USA and the Oak Ridge National Laboratory
in Tennessee, USA (International Union of Pure and Applied Chemistry, 2016). These elements are
still unnamed. According to the IUPAC rules for naming, names should relate to a mythological
concept, a mineral, a place or country, a property, or a scientist. The names of all new elements
must have the ending “-ium” for groups 1-16, “ine for elements of group 17 and “-on” for group 18
(International Union of Pure and Applied Chemistry, 2015). Discuss these new discoveries by
addressing one or both of the following questions:

1) What names would you propose for the new elements? Provide a rational based on
historical precedent or chemical importance for the names you propose.
2) Many newspaper headlines stated: “the Periodic Table is now complete”. Does the discovery
of these four new elements mark the end of the discovery of any further new elements?
Provide a solid rationale for your answer.

4) New Safety Standards in Canada

On June 1st, 2015, Canada adopted WHMIS 2015 to align the former Workplace Hazardous
Materials Information System with the Globally Harmonized System of Classification and Labelling
of Chemicals (GHS). The GHS calls for more clarity in the safe labelling of a wider variety of
substances; for example, the GHS includes specific symbols for classifying substances that
negatively impact the environment or human health.
Discuss chemical lab safety in your high school laboratory by addressing how educational
environments and industry create a culture of safety by enforcing WHMIS 2015 and other safety
precautions in the lab. Use specific situations to illustrate your points. You may also want to address
cost implications, training implications, the potential for green chemistry, and the responsibility of
students, teachers and schools/workplaces for ensuring safety in chemistry labs.
THE CANADIAN CHEMISTRY CONTEST 2016
for high school and CEGEP students
(formerly the National High School Chemistry Examination)

PART C: CANADIAN CHEMISTRY OLYMPIAD

Final Selection Examination 2016
Free Response Development Problems (90 minutes)
This segment has five (5) questions. While students are expected to attempt all questions for a
complete examination in 1.5 hours, it is recognized that backgrounds will vary and students will
not be eliminated fr om fur ther competition because they have missed par ts of the paper .
Your answers are to be written in the spaces provided on this paper. All of the paper, including
this cover page, along with a photocopy of Part A of the examination, is to be returned
IMMEDIATELY by courier to your Canadian Chemistry Olympiad Coordinator.

— PLEASE READ — PART A ( )

Correct Answers
1. BE SURE TO COMPLETE THE INFORMATION REQUESTED AT THE
BOTTOM OF THIS PAGE BEFORE BEGINNING PART C OF THE
EXAMINATION. 25 x 1.6 = .......... /040

2. STUDENTS ARE EXPECTED TO ATTEMPT ALL QUESTIONS OF

PART C
PART A AND PART C. CREDITABLE WORK ON A LIMITED
NUMBER OF THE QUESTIONS MAY BE SUFFICIENT TO EARN AN 1. ..................... /012
INVITATION TO THE NEXT LEVEL OF THE SELECTION PROCESS.
2. ..................... /012
3. IN QUESTIONS WHICH REQUIRE NUMERICAL CALCULATIONS, BE
SURE TO SHOW YOUR REASONING AND YOUR WORK.
3. ..................... /012

4. ..................... /012
4. ONLY NON-PROGRAMMABLE CALCULATORS MAY BE USED ON
THIS EXAMINATION. 5. ..................... /012

5. NOTE THAT A PERIODIC TABLE AND A LIST OF SOME PHYSICAL

City & Province ___________ Date of Birth

E-Mail ____________ Home Telephone ( ) - _

Years at a Canadian high school ___ No. of chemistry courses at a Québec CÉGEP ___

Male Canadian Citizen Landed Immigrant Visa Student 

Female 
Teacher __________________________ Teacher E-Mail ___________________________ 
1. (a). The partial pressure of oxygen in inhaled air (pO 2 (in)) = 159 mmHg, and in exhaled air
(pO 2 (ex)) = 116 mmHg. If the ambient air pressure is 760 mmHg, calculate how many grams of
O 2 are transferred from the atmosphere to our alveoli each minute at 298 K. Assume normal
breathing conditions of 10 inhalations per minute at 2.0 L each per inhalation.

3 marks

(b). Oxygen enters our bloodstream from our alveoli, where it binds to the oxygen-binding
protein hemoglobin (Hb). Hemoglobin has four oxygen-binding sites. One liter of fully
oxygenated blood can carry 0.18 L of O 2 measured at 310 K and 1 atm. Calculate how many
hemoglobin molecules are required to transport the O 2 in 1.0 L of fully oxygenated blood.

3 marks

-2-
(c). The equilibrium between hemoglobin and the O 2 in blood can be represented as:

Hb + O 2 ⇌ HbO 2

The equilibrium constant for this reaction is 9.2 x 1018.

Carbon monoxide (CO) also binds with hemoglobin in the following reaction:

Hb + CO ⇌ HbCO

This reaction has an equilibrium constant of 2.3 x 1023.

Determine the Gibbs energies of reaction for the above two processes at 37˚C, and indicate
whether each process favours the forward or reverse reaction.

4 marks

(d). Which equilibrium in part (c). lies further towards the products? Does your answer support
the argument that carbon monoxide is toxic? Provide an explanation for your answer.

2 marks
-3-
2. Chloropicrin, Cl 3 CNO 2 , is a volatile pesticide used in agricultural applications. Typically, soil
is sealed under a tarp and chloropicrin vapour is pumped into the airtight system and maintained
for three to seven days. During the First World War, chloropicrin proved an effective chemical
weapon, given that it was less lethal than phosgene (COCl 2 ).

Chloropicrin is prepared from the reaction of nitromethane and sodium hypochlorite.

(a). Determine the oxidation number of chlorine in sodium hypochlorite (NaOCl).

1 mark

(b). Given the unbalanced chemical equation below, determine the balanced chemical equation
for this reaction.

H 3 CNO 2 + NaOCl  Cl 3 CNO 2 + NaOH

1 mark

(c). State the chemical reaction type depicted in (b).

1 mark

(d). In 1937 at Queen’s University, Canadian professor E.W.R. Steacie and graduate student
Walter MacFarlane Smith demonstrated that chloropicrin thermally decomposed to form three
gases: phosgene, nitrogen(II) oxide and chlorine. Write a balanced chemical equation for this
reaction.

1 mark
-1
(e). The standard enthalpy of formation for chloropicrin is –78.6 kJ mol . Given the data
provided below, calculate the enthalpy change for the thermal decomposition reaction of
chloropicrin.

½N 2 (g) + ½O 2 (g)  NO(g) ∆ f H° = +90.3 kJ mol-1

C(s, graphite) + ½O 2 (g) + Cl 2 (g)  COCl 2 (g) ∆ f H° = –218.8 kJ mol-1

2 marks

-4-
(f). In 2009, a research group led by Dr. Abdelwahid Mellouki reported that chloropicrin, when
exposed to sunlight at ambient temperature and pressure, undergoes homolytic C–N
bond breakage to yield CCl 3 and NO 2 . Draw the Lewis (electron dot) structures of CCl 3 and
NO 2 .

1 mark

(g). Using VSEPR (valence shell electron-pair repulsion) theory, sketch the most probable
molecular structures for CCl 3 and NO 2 .

1 mark

(h). Given its pungent odor, chloropicrin has been used as warning agent, mixed with an odorless
fumigant compound (C) as a residential fumigant. The following industrial process outlines the
synthesis of C:

Combustion of finely divided element (A) in excess air yields a gaseous, binary compound (B)
which is an economically important chemical compound. At 325°C, in the presence of a catalyst,
chlorine gas and hydrogen fluoride, B is converted to the compound C, according to the
following balanced chemical equation:

Cl 2 + B + 2HF  C + 2HCl

In VSEPR “AXE format” (where E represents a lone pair of electrons), C has the molecular
geometry AX 4 , with a two-fold rotational axis of symmetry and two perpendicular planes of
symmetry (containing the two-fold rotational axis). C is 37.23% fluorine by mass.

Determine the molecular formula of A, B and C.

3 marks

(i). Using VSEPR theory, sketch the molecular structure of C.

1 mark
-5-
3. (a). Aldehydes and ketones react with alcohols to eventually form acetals and ketals.

O HO OCH3 CH3 O OCH3

C CH3 OH C CH3 OH C
H3 C R H3 C R H3 C R
+ a hemi-acetal R = H + an acetal R = H
an aldehyde R = H H H
a ketone R = CH3 a hemi-ketal R = CH3 a ketal R = CH3

A number of oxygen-containing functional groups are present in the structure below. Using the
example above as a guide, indicate the positions of the TWO aldehyde/ketone derivatives by
drawing an arrow to the carbon atoms of the former carbonyl (C=O). State whether the group is
a hemi-acetal, hemi-ketal, acetal or ketal.
H
O
O O H3 CO O CH3

O H
CH2 OCH3
HO
O
CH2 OCH3
CH3 H H
O
O OCH3

O
2 marks

(b). A resonance structure is one of several valence-bond structures with localized electrons that
approximate the true structure of a compound that has delocalized electrons. Complete the
templates below to show three major resonance structures of the ester shown by clearly adding
any missing bonds, lone pairs of electrons and formal charges that are present.

O O O
H H H H H H
C C C
H C O C H H C O C H H C O C H
H H H H H H

3 marks

-6-
(c). Optically active compounds are not superimposable upon their mirror images.
Three-dimensional awareness is important in predicting optical activity. Complete the structures
below by adding an H and an OH group to each unspecified bond to generate an optically active
and a non-optically active compound.

CH3 CH3
H OH H OH
= bond out of the page

= bond into the page

CH3 CH3

Optically Active NOT Optically Active

2 marks
(d). Place the following compounds in order of increasing acidity:
O O
CH3 CH2 C OH CH3 CH2 CH OH CH3 CH C OH CH3 CH2 NH2
CH3 Br
A B C D

least acidic most acidic

1 mark
(e). A compound that lacks a carbonyl group (C=O) and has the formula C14H24O reacts rapidly
with an excess of H2 in the presence of a catalyst to yield a new compound with the formula
C14H28O. The general formula of a non-cyclic alkane is C n H (2n+2) .

The ORIGINAL compound contained ring(s) and double bond(s)

2 marks
(f). Esters hydrolyze to form alcohols and carboxylic acids, whereas amides hydrolyze to form
amines and carboxylic acids. Write the products of the acidic aqueous hydrolysis of the
compound below that incorporates both an ester and an amide functionality.
O H2 O
+
CH3 CO2 H + CH 3 OH
H3 C OCH3 H , heat
ester

O H2 O
+
+
CH3 CO2 H + NH 4
H3 C NH2 H , heat
amide
O
O H2 O
N +
O CH3 H , heat

2 marks
-7-
4. The following procedure is used to determine the manganese content of various types of steel,
provided that the chromium content is low:

i. A solution of sodium hydrogen arsenite (Na 2 HAsO 3 ) is first prepared by dissolving

1.230 g of As 2 O 3 (M m 197.841 g mol–1) in concentrated aqueous sodium hydroxide,
neutralizing with hydrochloric acid, buffering with sodium bicarbonate, and finally
diluting to volume in a 1.000 L volumetric flask.

ii. Approximately 1 g of the steel sample is weighed accurately into a large conical flask, to
which is added a mixture of concentrated sulphuric, phosphoric, and nitric acids. The
solution is heated until the sample is fully dissolved and brown fumes cease to evolve.

iii. The solution is diluted with 50 mL of water, to which is added 5 mL of 0.1 M silver
nitrate and 2.5 g of ammonium persulphate. This mixture is boiled for 30 seconds and
cooled rapidly to below 25 °C. Any manganese in the sample is now present as MnO 4 –.

iv. A further 75 mL of water is added immediately, together with 5 mL of 0.2 M sodium

chloride.

v. The sample is titrated immediately with the sodium hydrogen arsenite solution to a clear
yellow end point that does not change upon further addition of the titrant.

(a). Calculate the concentration of the Na 2 HAsO 3 titrant obtained in step (i) to the correct
number of significant figures.

2 marks

(b). The silver ion in step (iii) acts as a catalyst for the ammonium persulphate; why is chloride
still added after destroying any residual persulphate?

2 marks

(c). Why would high chromium content in the steel interfere with this method?

2 marks

-8-
(d). Write the balanced equation for the titration reaction:

HAsO 3 2– + 2 MnO 4 – + H+→ HAsO 4 2– + 2 Mn2+ + H2O

2 marks

(e). An analyst tests a 0.9875 g sample of steel using this procedure, and obtains an end point
volume of 25.32 mL. What is the mass of manganese obtained from the steel sample? Show your
calculation for full marks.

4 marks

-9-
5. When H2S is dissolved in water it is almost saturated at a concentration near 0.1 M. Three
species containing sulfur exist in this solution (H2S, HS– and S2–). Their proportions depend on
the acidity of the solution. Given the following equilibrium constants:

H2S → H+ + HS– Ka1 = 1.0 x 10–7

HS– → H+ + S2– Ka2 = 1.3 x 10–13

(a). What is the concentration of the sulfide ion, [S2–], in a saturated 0.100 M solution of H2S
when the solution pH = 2.0?

5 marks

(b). A solution contains the cations Mn2+, Co2+, and Ag+ at an original concentration of 0.010M
each. Which of these ions will precipitate when the solution is saturated in H2S and the pH
adjusted to 2.0 by adding HCl? Explain your answer.

Given:
MnS Ksp = 2.5 x 10–10 CoS Ksp = 4.0 x 10–21 Ag2S Ksp = 6.3 x 10–50

3 marks

- 10 -
(c). How many grams of lead(II) sulfide, PbS, will precipitate from 1.00 L of a saturated solution
of lead(II) sulfate, PbSO4, if the concentration of sulfide ion, [S2–], is adjusted to give a
concentration of 1.00 x 10–17 M?

Given:
Pb SO4 Ksp = 1.6 x 10–8 PbS Ksp = 2.5 x 10–27

4 marks

--END OF PART C--

58 59 60 61 62 63 64 65 66 67 68 69 70 71
Ce Pr Nd Pm Sm Eu Gd Tb Dy Ho Er Tm Yb Lu
140.1 140.9 144.2 (145) 150.4 152.0 157.3 158.9 162.5 164.9 167.3 168.9 173.0 175.0

90 91 92 93 94 95 96 97 98 99 100 101 102 103

Th Pa U Np Pu Am Cm Bk Cf Es Fm Md No Lr
232.0 (231.0 (238.0) (237) (244) (243) (247) (247) (251) (252) (257) (258) (259) (262)

Symbol Value
Symbole Quantité numérique

Atomic mass unit amu 1.66054 x 10-27 kg Unité de masse atomique

1Å = 1 x 10-10 m STP/TPN SATP/TPAN

1 atm = 101.325 kPa 273.15 K 298 K
1 bar = 1 x 105 Pa 100 kPa 100 kPa
THE CANADIAN CHEMISTRY CONTEST 2016
PART A – MULTIPLE CHOICE QUESTIONS (60 minutes)
All contestants should attempt this part of the contest before proceeding to Part B and/or Part C
The only reference material allowed is the CIC/CCO Periodic Table provided. You must complete answers on the Scantron Sheet provided. A
scientific calculator is allowed. No phones or any devices that can be used for communication are allowed.

A) potassium permanganate B) sodium chlorate

A) 110 times B) 1100 times C) 510 times D) 700 times E) 51 times

A) Sc B) Y C) K D) Zn E) Ga
CCC 2016 page 2 of 4

A) ΔG⁰ rxn > 0 B)  S universe > 0 C)  S universe < 0

A) 5.4 x 10–2 mol L–1 B) 3.2 x 10–5 mol L–1 C) 6.4 x 10–5 mol L–1
D) ΔH⁰ rxn > 0 E) ΔH⁰ rxn < 0
D) 1.9 x 10–8 mol L–1 E) 1.2 x 10–9 mol L–1
CCC 2016 page 3 of 4

16) The transition metal rhenium (Re), is among the rarest elements in the 18) Solid lead carbonate precipitate can be formed from mixing aqueous
earth’s crust. The precursor to the pure metal, ammonium perrhenate, is lead nitrate and sodium carbonate:
produced during the refinement of molybdenum ores. The principal
application of rhenium is as an alloy with nickel, used in jet engine Pb(NO3)2 (aq) + Na2CO3 (aq)  PbCO3(s) + 2 NaNO3 (aq)
components. Consider the unbalanced chemical equation for the hydrogen
reduction of ammonium perrhenate: If 360 mL of 0.15 mol L–1 sodium carbonate was
combined with 45 mL of 0.60 mol L–1 lead nitrate,
__ NH4ReO4 + __ H2 __ Re + __H2O + __ NH3
which of the following diagrams best describes the
system once it has gone to completion? A
Assume the oxidation number of nitrogen in the reactants and products is
unchanged. Determine the sum of the smallest integer coefficients for the
stoichiometrically balanced chemical equation.

A) 5 B) 14 C) 18 D) 20 E) 21

mass of desired product

reaction mass efficiency =
(total input mass−mass of recycled material)

I. water II. hexane III. ethanol IV. hexanol

What is the percentage reaction mass efficiency for this process? A) 1.4 % B) 2.8 % C) 3.6 % D) 5.5 % E) 7.8%

A) 43.3 % B) 54.3% C) 70.9% D) 84.6 % E) 89.1%

CCC 2016 page 4 of 4

21) 2- propanol reacts with oxygen as follows: 23) A gaseous anesthetic with an unknown molecular formula is 85.63%
carbon and 14.37% hydrogen by mass. What is the molecular formula of
2 C3H7OH (l) + 9 O2 (g)  6 CO2 (g) + 8 H2O (g) the unknown if 0.45 L of the compound combusts with excess oxygen at
If 0.500 moles of 2-propanol react in the presence of 4.00 moles of oxygen, 120.0C at 72.93 kPa to form 2.70 L of an equimolar mixture of carbon
how many kilojoules of heat would be absorbed or released? A table of dioxide and water vapour?
average bond energies is given below.
A) C3H6 B) C4H8 C) C5H10 D) C6H12 E) C7H14
Bond Type Bond Energy Bond Type Bond Energy
(kJ mol–1) (kJ mol–1) 24) Given the following data table for the reaction 2 A + B2 → 2 AB
C-H 413 O=O 495
O-H 467 C=O 799 [A] mol L–1 [B2] mol L–1 Rate of Reaction (mol L–1 s–1)
C-O 358 C-C 347 0.100 0.100 0.117
0.200 0.100 0.468
A) – 1890 kJ B) + 1890 kJ C) – 1680 kJ 0.200 0.200 0.936
D) – 946 kJ E) + 473 kJ
What is the rate of reaction in mol L–1 s–1 if [A] = [B2] = 0.300 mol L–1?
22) For the cell depicted, the half-reactions are:
A) 1.87 B) 2.81 C) 3.02 D) 3.16 E) 3.51
Zn2+ (aq) + 2e– → Zn(s) E° = –0.76 V
Cu2+ (aq) + 2e– → Cu(s) E° = +0.34 V
25) Flask 1 Flask 2
Which of the following is true for the spontaneous cell reaction? 2.0 g of H2 16.0 g of O2
gas at 25C gas at 25C
A) Zn is the anode; the electron flow is from anode to cathode; anions
and P1 and P2
migrate through the salt bridge from the Zn/Zn2+ to the Cu/Cu2+
half-cell and cations migrate in the opposite direction. Both Flask 1 and Flask 2 have a volume of exactly 2.0 L, KE is the average
B) Zn is the cathode; the electron flow is from anode to cathode; kinetic energy, and P is pressure. Which statement below is TRUE?
anions migrate through the salt bridge from the Zn/Zn2+ to the
Cu/Cu2+ half-cell and cations migrate in the opposite direction.
A) P1 = P2
C) Zn is the anode; the electron flow is from cathode to anode; anions
B) the KE of the particles in flask 1 < the KE of the particles in flask 2
migrate through the salt bridge from the Zn/Zn2+ to the Cu/Cu2+
half-cell and cations migrate in the opposite direction. C) the number of particles in flask 1 > the number of particles in flask 2
D) Zn is the cathode; the electron flow is from anode to cathode; D) the number of collisions in flask 1 = number of collisions in flask 2
cations migrate through the salt bridge from the Zn/Zn2+ to the E) 2 P1 = P2
Cu/Cu2+ half-cell and anions migrate in the opposite direction.
E) Zn is the anode; the electron flow is from anode to cathode;
cations migrate through the salt bridge from the Zn/Zn2+ to the
End of Part A of the contest
Cu/Cu2+ half-cell and anions migrate in the opposite direction.
Go back and check your work
Rubric guideline for evaluating the CCC (Part B) essay topics
For a total mark out of 20 points

Criteria 4 marks 3 marks 2 marks 1 mark

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