M14/4/CHEMI/SP2/ENG/TZ2/XX

22146117

CHEMISTRY Candidate session number

standard level
Paper 2

Monday 19 May 2014 (afternoon) Examination code

1 hour 15 minutes 2 2 1 4 – 6 1 1 7

INSTRUCTIONS TO CANDIDATES

• Write your session number in the boxes above.

• Do not open this examination paper until instructed to do so.
• Section A: answer all questions.
• Section B: answer one question.
• Write your answers in the boxes provided.
• A calculator is required for this paper.
• A clean copy of the Chemistry Data Booklet is required for this paper.
• The maximum mark for this examination paper is [50 marks].

22 pages
© International Baccalaureate Organization 2014

24EP01
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Section a

Answer all questions. Write your answers in the boxes provided.

1. A class studied the equilibrium established when ethanoic acid and ethanol react together
in the presence of a strong acid, using propanone as an inert solvent. The equation is
given below.

CH 3COOH + C2 H 5OH  CH 3COOC2 H 5 + H 2 O

One group made the following initial mixture:

Liquid Volume / cm3

Ethanoic acid 5.00 ± 0.05

Ethanol 5.00 ± 0.05

6.00 mol dm–3 aqueous hydrochloric acid 1.00 ± 0.02

Propanone 39.0 ± 0.5

(a) The density of ethanoic acid is 1.05 g cm–3. Determine the amount, in mol, of ethanoic
acid present in the initial mixture. [3]

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(b) The hydrochloric acid does not appear in the balanced equation for the reaction. State
its function. [1]

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24EP02
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(Question 1 continued)

(c) Identify the liquid whose volume has the greatest percentage uncertainty. [1]

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(d) After one week, a 5.00 ±  0.05 cm3 sample of the final equilibrium mixture was pipetted
out and titrated with 0.200 mol dm–3 aqueous sodium hydroxide to determine the amount
of ethanoic acid remaining. The following titration results were obtained:

Titration number 1 2 3

Initial reading / cm3 ± 0.05 1.20 0.60 14.60

Final reading / cm3 ± 0.05 28.80 26.50 40.70

Titre / cm3 27.60 25.90 26.10

(i) Calculate the absolute uncertainty of the titre for Titration 1 (27.60 cm3). [1]

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Suggest the average volume of alkali, required to neutralize the 5.00 cm3 sample,
(ii)
that the student should use. [1]

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24EP03
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(Question 1 continued)

23.00 cm3 of this 0.200 mol dm–3 aqueous sodium hydroxide reacted with the

(iii)
ethanoic acid in the 5.00 cm3 sample. Determine the amount, in mol, of ethanoic
acid present in the 50.0 cm3 of final equilibrium mixture. [2]

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(e) Referring back to your answer for part (a), calculate the percentage of ethanoic acid
converted to ethyl ethanoate. [1]

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(f) Deduce the equilibrium constant expression for the reaction. [1]

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(g) Outline how you could establish that the system had reached equilibrium at the end of
one week. [1]

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24EP04
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(Question 1 continued)

(h) Outline why changing the temperature has only a very small effect on the value of the
equilibrium constant for this equilibrium. [1]

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(i) Outline how adding some ethyl ethanoate to the initial mixture would affect the
amount of ethanoic acid converted to product. [2]

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(j) Propanone is used as the solvent because one compound involved in the equilibrium is
insoluble in water. Identify this compound and explain why it is insoluble in water. [2]

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(k) Suggest one other reason why using water as a solvent would make the experiment
less successful. [1]

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24EP05
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2. Boron is most often encountered as a component in borosilicate glass (heat resistant glass).
The naturally occurring element contains two stable isotopes,105 B and 115 B.

(a) State the number of protons, neutrons and electrons in an atom of 115 B.

Protons Neutrons Electrons

11
B
5
[1]

(b) The relative atomic mass of boron is 10.8, to three significant figures. Calculate the
percentage of 105 B in the naturally occurring element. [2]

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(c) Isotopes of boron containing 7 and 8 neutrons also exist. Suggest why releasing isotopes
containing more neutrons than the stable isotope into the environment can be dangerous. [1]

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(d) (i) State the formula of the compound that boron forms with fluorine. [1]

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(This question continues on the following page)

24EP06
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(Question 2 continued)

(ii)
Explain why this compound acts as a Lewis acid. [2]

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24EP07
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3. Hydrocarbons, such as nonane, C9H20 , are essential as fuels and as raw materials.

(a) State a balanced equation for the complete combustion of nonane. [2]

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(b) Combustion also often forms carbon and carbon monoxide. Outline what reaction
conditions result in these being produced. [1]

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(c) Propene, which can be obtained from nonane, can be polymerized.

(i) State the type of polymerization that occurs. [1]

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Draw the structure of a segment of the polymer containing six carbon atoms.
(ii) [1]

24EP08
 –9– M14/4/CHEMI/SP2/ENG/TZ2/XX

Section b

Answer one question. Write your answers in the boxes provided.

4. Group 7 of the periodic table contains a number of reactive elements such as chlorine, bromine
and iodine.

(a) (i) Describe the colour change that occurs when aqueous chlorine is added to aqueous
sodium bromide. [1]

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(ii)
Outline, with the help of a chemical equation, why this reaction occurs. [2]

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(b) The colour change in the reaction between aqueous chlorine and aqueous sodium iodide
is very similar, but it differs with an excess of aqueous chlorine. Describe the appearance
of the reaction mixture when excess aqueous chlorine has been added to aqueous
sodium iodide. [1]

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(This question continues on the following page)

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24EP09
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(Question 4 continued)

(c) Bleaches in which chlorine is the active ingredient are the most common, although some
environmental groups have concerns about their use. In aqueous chlorine the equilibrium
below produces chloric(I) acid (hypochlorous acid), HOCl, the active bleach.

Cl2 (aq) + H 2 O (l)  HOCl (aq) + H + (aq) + Cl− (aq)

(i) Chloric(I) acid is a weak acid, but hydrochloric acid is a strong acid. Outline how
this is indicated in the equation above. [1]

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(ii) State a balanced equation for the reaction of chloric(I) acid with water. [1]

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(iii)
Outline, in terms of the equilibrium above, why it is dangerous to use an acidic
toilet cleaner in combination with this kind of bleach. [2]

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(iv)
Suggest why a covalent molecule, such as chloric(I) acid, is readily soluble in water. [2]

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24EP10
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(Question 4 continued)

(v) Draw the Lewis (electron dot) structure of chloric(I) acid. [1]

(vi)
Predict the H–O–Cl bond angle in this molecule and explain this in terms of the
valence shell electron pair repulsion (VSEPR) theory. [3]

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(d) Aqueous sodium chlorate(I), NaOCl, the most common active ingredient in chlorine
based bleaches, oxidizes coloured materials to colourless products while being reduced
to the chloride ion. It will also oxidize sulfur dioxide to the sulfate ion.

(i) Deduce the coefficients required to balance the half-equations given below. [2]

___ ClO − + ___ H + + ___ e −  ___ H 2 O + ___ Cl−

___ SO 24− + ___ H + + ___ e −  ___ SO 2 + ___ H 2 O

(This question continues on the following page)

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24EP11
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(Question 4 continued)

(ii)
State the initial and final oxidation numbers of both chlorine and sulfur in the
equations in part (i). [2]

Element Initial oxidation number Final oxidation number

Chlorine
Sulfur

(iii)
Use the half-equations to deduce the balanced equation for the reaction between
the chlorate(I) ion and sulfur dioxide. [2]

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24EP12
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5. A group of students investigated the rate of the reaction between aqueous sodium thiosulfate
and hydrochloric acid according to the equation below.

Na 2S2 O3 (aq) + 2HCl (aq) → 2NaCl (aq) + SO 2 (g) + S(s) + H 2 O(l )

The two reagents were rapidly mixed together in a beaker and placed over a mark on a piece
of paper. The time taken for the precipitate of sulfur to obscure the mark when viewed through
the reaction mixture was recorded.

HCl + Na2S2O3

Mark

Initially they measured out 10.0 cm3 of 0.500 mol dm–3 hydrochloric acid and then added
40.0 cm3 of 0.0200 mol dm–3 aqueous sodium thiosulfate. The mark on the paper was obscured
47 seconds after the solutions were mixed.

(a) The teacher made up 2.50 dm3 of the sodium thiosulfate solution using sodium thiosulfate
pentahydrate crystals, Na 2S2O3•5H2O. Calculate the required mass of these crystals. [3]

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24EP13
 – 14 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 5 continued)

(b) The teacher asked the students to measure the effect of halving the concentration of
sodium thiosulfate on the rate of reaction.

(i) State the volumes of the liquids that should be mixed. [1]

Liquid 0.500 mol dm–3 HCl 0.0200 mol dm–3 Na 2S2O3 Water

Volume / cm3

(ii)
State why it is important that the students use a similar beaker for both reactions. [1]

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(iii)
Explain, in terms of the collision theory, how decreasing the concentration of
sodium thiosulfate would affect the time taken for the mark to be obscured. [2]

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24EP14
 – 15 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 5 continued)

(c) (i) Sketch and label, indicating an approximate activation energy, the
Maxwell–Boltzmann energy distribution curves for two temperatures, T1 and T2
(T2 > T1), at which the rate of reaction would be significantly different. [3]

(ii)
Explain why increasing the temperature of the reaction mixture would
significantly increase the rate of the reaction. [3]

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24EP15
 – 16 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 5 continued)

(d) The teacher asked the students to devise another technique to measure the rate of this
reaction.

(i) One group suggested recording how long it takes for the pH of the solution to
change by one unit. Calculate the initial pH of the original reaction mixture. [2]

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(ii)
Deduce the percentage of hydrochloric acid that would have to be used up for the
pH to change by one unit. [1]

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24EP16
 – 17 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 5 continued)

(e) Another group suggested collecting the sulfur dioxide and drawing a graph of the volume
of gas against time.

(i) Calculate the volume of sulfur dioxide, in cm3, that the original reaction mixture
would produce if it were collected at 1.00 ×105 Pa and 300 K. [3]

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(ii)
Suggest why it is better to use a gas syringe rather than collecting the gas in a
measuring cylinder over water. [1]

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Turn over
24EP17
 – 18 – M14/4/CHEMI/SP2/ENG/TZ2/XX

6. Alkenes, such as A (shown below), are important intermediates in the petrochemical industry
because they undergo addition reactions to produce a wide variety of products, such as the
conversion shown below.

H 3C H3C CH3
CH3
C C H C C Br
H3C CH3
H3C CH3
A B

(a) Applying IUPAC rules, state the name of A. [1]

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(b) State the reagent required to convert A into B. [1]

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24EP18
 – 19 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 6 continued)

(c) Another way to make B is the reaction shown below.

H 3C CH3 H3C CH3

H C C H + Br2 H C C Br + HBr

H 3C CH3 H3C CH3

(i) State the conditions required for this reaction to occur. [1]

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(ii)
Outline why it would give a poor yield of the desired product. [1]

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(d) B can be converted into C.

H 3C CH3

H C C OH

H 3C CH3
C

(i) State the reagent required. [1]

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24EP19
 – 20 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 6 continued)

(ii)
Explain the mechanism of this reaction, using curly arrows to represent the
movement of electron pairs. [3]

(e) A can also be converted into C without going via B. State the reagent and conditions
required. [2]

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(f) (i) State why C is not readily oxidized by acidified potassium dichromate(VI). [1]

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24EP20
 – 21 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 6 continued)

Deduce the structural formula of an isomer of C that could be oxidized to a

(ii)
carboxylic acid by this reagent. [1]

(g) In the gas phase, A reacts with hydrogen to form D.

H 3C H3C CH3
CH3
C C + H2 H C C H
H 3C CH3
H3C CH3
A D

(i) State the conditions required for this reaction to occur. [1]

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State the homologous series to which D belongs.

(ii) [1]

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24EP21
 – 22 – M14/4/CHEMI/SP2/ENG/TZ2/XX

(Question 6 continued)

Determine the enthalpy change, in kJ mol–1, for the reaction of A with hydrogen,
(iii)
using Table 10 of the Data Booklet, and state whether the reaction is exothermic
or endothermic. [4]

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The standard enthalpy change of combustion of A is – 4000 kJ mol–1. Calculate the

(iv)
amount of A, in mol, that would have to be burned to raise the temperature of 1 dm3
of water from 20 °C to 100 °C . [2]

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24EP22
Please do not write on this page.

Answers written on this page

will not be marked.

24EP23
Please do not write on this page.

Answers written on this page

will not be marked.

24EP24