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UNIVERSITY OF CAMBRIDGE INTERNATIONAL EXAMINATIONS

General Certificate of Education
Advanced Subsidiary Level and Advanced Level
*1253499376*

CHEMISTRY 9701/22
Paper 2 Structured Questions AS Core May/June 2013
1 hour 15 minutes
Candidates answer on the Question Paper.
Additional Materials: Data Booklet

READ THESE INSTRUCTIONS FIRST

Write your Centre number, candidate number and name on all the work you hand in.
Write in dark blue or black pen.
You may use a soft pencil for any diagrams, graphs or rough working.
Do not use staples, paper clips, highlighters, glue or correction fluid.
DO NOT WRITE IN ANY BARCODES.

Answer all questions.

Electronic calculators may be used.
You may lose marks if you do not show your working or if you do not use appropriate units.
A Data Booklet is provided.

At the end of the examination, fasten all your work securely together.
The number of marks is given in brackets [ ] at the end of each question or part question.

For Examiner’s Use

Total

This document consists of 11 printed pages and 1 blank page.

IB13 06_9701_22/3RP
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Answer all the questions in the spaces provided. Examiner’s
Use

1 Ammonium sulfate is a fertiliser which is manufactured by the reaction between ammonia

and sulfuric acid.

(a) Ammonia is described as a weak base and sulfuric acid as a strong acid.

By using an equation, explain clearly what is meant by the term weak base.

...........................................................................................................................................

...........................................................................................................................................

...........................................................................................................................................

...........................................................................................................................................

..................................................................................................................................... [3]

(b) Ammonia and sulfuric acid are both manufactured by processes which involve chemical
equilibria.

(i) Sulfuric acid is produced from sulfur trioxide which is made by the Contact process.

State three important operating conditions for the Contact process for the
manufacture of sulfur trioxide.

For each of your conditions, you should avoid the use of vague phrases such as
‘high temperature’.

condition 1 .................................................................................................................

....................................................................................................................................

condition 2 .................................................................................................................

....................................................................................................................................

condition 3 .................................................................................................................

....................................................................................................................................

(ii) How is the sulfur trioxide produced converted into sulfuric acid?

....................................................................................................................................

....................................................................................................................................
[4]

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(c) Chloropropanols such as 1,3-dichloropropan-2-ol (1,3-DCP) are present in some foods. Examiner’s
Use
Cl CH2CH(OH)CH2Cl

1,3-DCP

(i) What will be produced when 1,3-DCP is reacted separately with the following
reagents under suitable conditions?
In each case give the structural formula.

concentrated sulfuric acid

an excess of ammonia

(ii) Describe as fully as you can what type of reaction occurs with ammonia.

....................................................................................................................................
[4]

[Total: 11]

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2 Chile saltpetre is a mineral found in Chile and Peru, and which mainly consists of sodium Examiner’s
nitrate, NaNO3. The mineral is purified to concentrate the NaNO3 which is used as a fertiliser Use
and in some fireworks.

In order to find the purity of a sample of sodium nitrate, the compound is heated in NaOH(aq)
with Devarda's alloy which contains aluminium. This reduces the sodium nitrate to ammonia
which is boiled off and then dissolved in acid.

3NaNO3(aq) + 8Al (s) + 5NaOH(aq) + 18H2O(l) → 3NH3(g) + 8NaAl (OH)4(aq)

The ammonia gas produced is dissolved in an excess of H2SO4 of known concentration.

2NH3 + H2SO4 → (NH4)2SO4

The amount of unreacted H2SO4 is then determined by back-titration with NaOH of known
concentration.

H2SO4 + 2NaOH → Na2SO4 + 2H2O

(a) A 1.64 g sample of impure NaNO3 was reacted with an excess of Devarda's alloy.
The NH3 produced was dissolved in 25.0 cm3 of 1.00 mol dm–3 H2SO4.
When all of the NH3 had dissolved, the resulting solution was titrated with NaOH(aq).
For neutralisation, 16.2 cm3 of 2.00 mol dm–3 NaOH were required.

(i) Calculate the amount, in moles, of H2SO4 present in the 25.0 cm3 of 1.00 mol dm–3
H2SO4.

(ii) Calculate the amount, in moles, of NaOH present in 16.2 cm3 of 2.00 mol dm–3 NaOH.

(iii) Use your answer to (ii) to calculate the amount, in moles, of H2SO4 that reacted with
16.2 cm3 of 2.00 mol dm–3 NaOH.

(iv) Use your answers to (i) and (iii) to calculate the amount, in moles, of H2SO4 that
reacted with the NH3.

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(v) Use your answer to (iv) to calculate the amount, in moles, of NH3 that reacted with Examiner’s
the H2SO4. Use

(vi) Use your answer to (v) to calculate the amount, in moles, of NaNO3 that reacted with
the Devarda's alloy.

(vii) Hence calculate the mass of NaNO3 that reacted.

(viii) Use your answer to (vii) to calculate the percentage by mass of NaNO3 present in
the impure sample.
Write your answer to a suitable number of significant figures.

[9]

(b) The above reaction is an example of a redox reaction.

What are the oxidation numbers of nitrogen in NaNO3 and in NH3?

NaNO3 ....................... NH3 ....................... [1]

[Total: 10]

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3 This question refers to the elements in the section of the Periodic Table shown below. Examiner’s
Use

H He
Li Be B C N O F Ne
Na Mg Al Si P S Cl Ar
K Ca ................. transition elements ................. Ga Ge As Se Br Kr

(a) From this list of elements, identify in each case one element that has the property
described. Give the symbol of the element.

(i) An element that when placed in cold water sinks and reacts readily.

...........

(ii) An element whose molecules contain π bonding.

...........

(iii) An element that forms a gaseous toxic oxide.

...........

(iv) The element which has a giant molecular structure and forms an oxide which also
has a giant molecular structure.

...........

(v) An element that forms a covalent chloride which dissolves in water to give a
conducting solution.

...........

(vi) The element in Period 3 (Na to Ar) with the greatest electrical conductivity.

...........
[6]

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(b) Some of the elements in Period 3 (Na to Ar) burn with a coloured flame when heated in Examiner’s
oxygen or chlorine. Use

(i) Give the symbol of one such element, the formula of the oxide formed, and state the
flame colour that would be seen.

symbol of element ....................................

formula of oxide ....................................

flame colour ....................................

(ii) For the element you have used in (i), give the formula of the chloride formed, and
state the pH of the solution produced when this chloride is shaken with water.

formula of chloride ....................................

pH of solution ....................................
[4]

(c) Chlorine reacts with both bromine and iodine to form BrCl and ICl respectively.
The melting points of chlorine and the two chlorides are shown in the table.

substance Cl 2 BrCl ICl

m.p. / °C –101 –66 24

(i) Showing outer electrons only draw a 'dot-and-cross' diagram of the bonding in ICl .

(ii) Suggest why the melting points increase from Cl 2 to ICl .

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................

(iii) Suggest which of these three molecules has the largest permanent dipole.
Explain your answer.

....................................................................................................................................

....................................................................................................................................

....................................................................................................................................
[5]

[Total: 15]

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4 Crotyl alcohol, CH3CH=CHCH2OH, is a colourless liquid which is used as a solvent. Examiner’s
Use
(a) In the boxes below, write the structural formula of the organic compound formed when
crotyl alcohol is reacted separately with each reagent under suitable conditions.
If you think no reaction occurs, write 'NO REACTION' in the box.

Br2 in an inert organic

A
solvent

B PCl 5

C H2 and Ni catalyst

D NaBH4

K2Cr2O7 / H+
E
heat under reflux

[5]

(b) Draw the displayed formula of the organic compound formed when crotyl alcohol is
reacted with cold, dilute acidified potassium manganate(VII).

[1]

(c) Draw the skeletal formula of the compound formed in reaction E.

[2]

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(d) Crotyl alcohol is obtained from crotonaldehyde, CH3CH=CHCHO. Examiner’s
Use
(i) Describe one test that would confirm the presence of a small amount of unreacted
crotonaldehyde in the crotyl alcohol.
Give the name of the reagent used and state what you would see.

reagent ......................................................................................................................

observation ................................................................................................................

(ii) What type of reaction is the conversion of crotonaldehyde into crotyl alcohol?

....................................................................................................................................
[3]

(e) Compound P, another unsaturated compound, is found in some blue cheeses.

The percentage composition by mass of compound P is C: 73.7%; H: 12.3%; O: 14.0%.

Calculate the empirical formula of compound P.

[2]

[Total: 13]

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5 A student reacted together an alcohol and a carboxylic acid under appropriate conditions to Examiner’s
produce an ester. Use
A sweet smelling organic liquid, Q, with the empirical formula C2H4O was produced.
The Mr of Q was found by experiment to be 87.5.

(a) What is the molecular formula of Q?

..................................................................................................................................... [1]

(b) In the boxes below, draw the structural formulae of four isomers with this formula that
are esters.

W X

Y Z

[4]

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A sample of Q was hydrolysed by heating with aqueous sulfuric acid. Examiner’s
The resulting mixture was heated under reflux with acidified potassium dichromate(VI) to Use
give a single organic product, R.
The product, R, was collected and subjected to the following tests.

A sample of R gave no reaction with Tollens’ reagent.

A second sample of R gave no reaction with 2,4-dinitrophenylhydrazine reagent.

A third sample of R gave an effervescence with sodium carbonate.

(c) (i) What does the result of the test with Tollens’ reagent show about R?

....................................................................................................................................

(ii) What does the result of the test with 2,4-dinitrophenylhydrazine reagent show about
R?

....................................................................................................................................

(iii) What functional group does the result of the test with sodium carbonate show to be
present in R?

....................................................................................................................................
[3]

(d) (i) What is the identity of the single organic compound, R?

............................................

(ii) Which of your structures, W, X, Y or Z, represents the ester, Q?

..................
[2]

(e) Which, if any, of your esters, W, X, Y or Z, is chiral?

...........................................................................................................................................

..................................................................................................................................... [1]

[Total: 11]

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