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1. (i) Large amounts of used film are disposed of every year.

After the silver


halide has been removed from the film, the remaining polymer sheets can be
disposed of by burning or by burying them in the ground.

Give one advantage for each method relative to the other.

burning ...........................................................................................................

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burying ...........................................................................................................

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[2]

(ii) Chemists are developing methods to convert some waste polymers into useful
chemicals.

Polyesters can be broken down by hydrolysis into organic acids and alcohols.

Give the conditions and reagent used for hydrolysing an ester link.

conditions ......................................................................................................

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

Bishop Thomas Grant School 1


(iii) Unused silver bromide can be recovered from waste films.

The amount of silver bromide in a sample can be determined by oxidising the


– –
bromide ions (Br ) to bromine (Br2), using bromate(V) ions (BrO3 ) as the
oxidising agent.

Give an overall balanced equation for this redox reaction by combining the half-
equations given below.
– –
2Br (aq) →Br2(aq) + 2e

– + –
2BrO3 (aq) + 12H (aq) + 10e →Br2(aq) + 6H2O(l)

working space

[2]
[Total 6 marks]

2. Zinc is a d-block element.

Complete the electronic configuration for zinc and explain why it does not readily form
3+
Zn ions.

Zn 1s2 2s2 2p6 ........ ........ ........ ........

explanation

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[Total 3 marks]

Bishop Thomas Grant School 2


3. Polyesters have become the major group of condensation polymers manufactured at
present. There is an increasing demand for PBT, a polymer used in making mouldings
for cars. PBT is made using the two monomers shown below.

O O

O H
H O O H H O

(a) (i) Explain why the formation of PBT is an example of


condensation polymerisation.

condensation ........................................................................................

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polymerisation ......................................................................................

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[2]

(ii) Complete the diagram below to show the structural formula of the repeating
unit for the polyester, PBT.

[2]

(iii) The monomers in (ii) are joined by ester links. Draw the full structural
formula of an ester link.

[1]

Bishop Thomas Grant School 3


(b) At very low temperatures, mouldings made from PBT become brittle. Explain why
thermoplastic (thermosoftening) polymers become brittle when their temperature
is lowered.

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[3]

(c) Describe two ways that chemists can modify a polymer, such as PBT to make it
more flexible.

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[2]
[Total 10 marks]

Bishop Thomas Grant School 4


4. X-ray film is made by coating a plastic sheet with a silver halide. The plastic sheet is
made from a mixture of a polyester and a nylon.

(a) A typical polyester used in the making of films is PET. A repeating unit is shown
below.

O O

O O

P E T

Draw the full structural formula of the alcohol used as a monomer to make PET.

[2]

(b) A nylon can be made by polymerising a mixture of the monomers D and E.

HOOC(CH2)4COOHH2N(CH2)6NH2
D E

(i) Give the systematic name of compound E.

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[2]

(ii) Nylon polymers are formed by a condensation reactions. Use the reaction
between compounds D and E to explain the meaning of condensation.

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[2]

Bishop Thomas Grant School 5


(c) Nylon is added to polyester to make X-ray film stronger. Explain, in terms of
intermolecular attractions, why the addition of nylon strengthens the film.

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[2]
[Total 8 marks]

5. Titanium alloys are often used for reaction vessels in the chemical industry because of
their high chemical resistance. However, they cannot be used with concentrated
hydrochloric acid. This reacts with titanium to form a mixture of coloured ions.

(i) One of the coloured ions formed when titanium reacts with hydrochloric acid is
3+
the hexaaquatitanium(III) ion, [Ti(H2O)6] (aq).

In the box below, draw the shape of this complex ion indicating the charge on the
ion.

Give the name for the shape of this complex ion.

shape of complex ion ......................................................


[3]

Bishop Thomas Grant School 6


+
(ii) The [Ti(H2O)4Cl2] ion is also formed in concentrated hydrochloric acid. Suggest
why there are two possible structures for this ion.

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[2]
[Total 5 marks]

Bishop Thomas Grant School 7


6. In this question, one mark is available for the quality of spelling, punctuation and
grammar.

A solid sample is thought to be impure acetanilide. The sample is soluble in ethanol.

Describe how thin-layer chromatography would be carried out to show that acetanilide
is present in the sample.

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[6]
Quality of Written Communication [1]
[Total 7 marks]

Bishop Thomas Grant School 8


4–
7. The reaction of edta ions with nickel(II) ions can be represented by the following
equation.
2+ 4– 2–
[Ni(H2O)6] (aq) + edta (aq) [Ni(edta)] (aq) + 6H2O(l)

The amount of nickel(II) ion in a solution can be found by titrating with a solution of
4–
edta of known concentration using a suitable indicator.
3 3
25.0 cm of a solution containing nickel(II) ions reacted with exactly 22.0 cm of a
–3 4–
0.100 mol dm solution of edta ions.

Calculate the concentration of nickel(II) ions in the solution.

Give your answer to an appropriate number of significant figures.

–3
concentration = ......................................... mol dm
[Total 4 marks]

Bishop Thomas Grant School 9


8. Xenical is a new weight-control drug for the long-term treatment of obesity. The active
ingredient in Xenical is a compound, called orlistat, whose structure is shown below. R
represents a carbon chain containing a functional group.

R
O

H N O

C O

H
o r l i s t a t

The group R in orlistat contains an ester group.

(i) Explain how molecules absorb infrared radiation.

Describe how infrared spectra can be used to show the presence of particular
functional groups.

Give details of any absorption peaks you would look for in the infrared spectrum
of an ester.

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[4]

Bishop Thomas Grant School 10


(ii) Hydrolysis of the ester group in group R using alkaline conditions gives
compound C.

The infrared spectrum of compound C is shown below. Identify the functional


group present in compound C. Give a reason for your answer.

1 0 0

t r a n s m i t t a n c e / %
8 0

6 0

4 0

2 0

4 0 0 0 3 0 0 0 2 0 0 0
w a v e n u –
m1 b e r / c m

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[2]
[Total 6 marks]

9. Unwanted metals can find their way into food, either from the soil or from machinery
during harvesting and processing. Ions of metals such as copper, iron and nickel
catalyse the breakdown of fats in food.

(a) Copper, iron and nickel are transition metals. What property of transition metals
allows them to behave as catalysts?

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

Bishop Thomas Grant School 11


(b) A class of food additives known as sequestrants can be used to remove these
metal ions.

Typical sequestrants are the calcium and sodium salts of H4 edta.

4–
The structure of the edta ion is shown below.
– –
O O 2 CC H 2 C O O C
N C 2H N C 2H
– O O C H C –C
2 C 2H O O

4–
The edta ion acts as a hexadentate ligand. On the structure above, label with
an asterisk (*) the six sites that form bonds to the metal ion.
[2]

(c) Underline the term below that describes the shape of the complex formed
4–
between a nickel(II) ion and an edta ion.

linear octahedralsquare planar tetrahedral


[1]
[Total 4 marks]

3+
10. In aqueous solutions, V ions form octahedral complex ions which have a green
colour.
3+
(i) Draw a three dimensional structure for these hydrated V ions, showing clearly
how the ligands bond to the cation.

[2]

Bishop Thomas Grant School 12


(ii) By drawing arrows in the appropriate boxes, complete the outer electron
3+
structures for V and V .

3d 4s

3+
V

[2]
[Total 4 marks]

11. Blue-green crystals, a mixture of copper(II) ethanoate salts, were used by artists in the
15th–18th centuries as pigments in paints. These crystals form on copper and copper-
containing alloys when the metal is left exposed to air under suitable conditions.

Copper plates were supported over vats containing boiling vinegar (ethanoic acid). In
the process, copper is converted into a mixture of copper(I) and copper(II) oxides which
then react to form copper(II) ethanoate.

(a) (i) Complete the electron configuration for a Cu atom.

1s2 2s2 2p6 ..........................................................


[2]

(ii) State from which sub-shell the electron is lost when a Cu atom forms a
Cu(I) ion.

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

(iii) Give the formula of the ethanoate ion.

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[1]

Bishop Thomas Grant School 13


(b) Copper(II) ethanoate dissolves in water to form a brightly coloured blue-green
solution. This was used to colour the seas in old maps.

Various shades of blue and green can be obtained by adding other chemicals to
this solution.

(i) On diluting the solution with water a pale blue colour forms. The complex
2+
ion, [Cu(H2O)6] , is now present in the solution.

Draw a structure to show clearly the shape of this complex ion.

Indicate clearly the type of bonding involved.

[4]

(ii) Addition of a small amount of ammonia solution to this pale blue solution
causes a pale blue precipitate to form.

Write an ionic equation, including state symbols, for the precipitation


reaction.

[2]

(iii) What would you see if an excess of ammonia was shaken with the blue
precipitate?

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[2]

Bishop Thomas Grant School 14


(c) Explain why a blue solution looks blue.

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[2]
[Total 14 marks]

12. In the 1930s, chemists began to design polymers that had similar structures to those
found In natural fibres. The first of these polymers, nylon-6,6, was quickly followed by
the invention of nylon-6.

(a) Suggest a reason why chemists wanted to find synthetic replacements for some
natural fibres.

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

(b) The repeating unit of nylon-6 is shown below.

H O

N ( C 2 H5 C )
n

Draw the structure of a monomer which can be used to make nylon-6.

[2]

Bishop Thomas Grant School 15


(c) At the same time that nylon-6,6 was invented, chemists also made a sample of a
nylon by reacting hexanedioic acid with compound A. The nylon was found to
have a low molecular mass and was therefore not developed any further.

N 2H

H 2 N

c o m p o u n d A

(i) Name compound A.

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[2]

(ii) Because of its low molecular mass, certain properties of the new nylon are
different from those of nylon-6. Describe how two of these properties are
different from those of nyion-6.

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[2]

(d) Recently, chemists have been able to make samples of a polymer using
4
compound A, but having a much higher Mr of 3 × 10 . The polymer was named
Stanyl and is stronger and has a higher melting point than either nylon-6,6 or
nylon-6. It is now used in manufacturing parts for car engines.

O O

C ( C 2 H4 C ) N ( C 2 H4 N )

H H

r e p e a t i n Sg t ua n iy t l o f

Bishop Thomas Grant School 16


(i) Approximately how many repeating units are there in a molecule of Stanyl?

number of repeating units = .........................................


[2]

(ii) Name the functional group connecting the repeating units in Stanyl.

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[1]

(iii) Explain why the melting point of Stanyl is higher than that of nylon-6,6
which has a similar molecular mass.

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[3]

(e) The manufacturers of Stanyl state that ‘as with all other polyamides, Stanyl is
attacked by strong mineral acids and absorbs polar solvents’.

(i) Draw the structures of the two organic products formed when Stanyl Is
hydrolysed with a strong acid. (The structure of Stanyl is repeated below.)

[2]

Bishop Thomas Grant School 17


(ii) Show using the diagram below how part of a Stanyl chain can form an
intemolecular bond with a water molecule. Show any partial charges.

O O

C ( C 2 H4 C ) N ( C 2 H4 N )

H H

[2]
[Total 17 marks]

Bishop Thomas Grant School 18


13. Ropemakers, who supply products for the modernisation of working sailing ships, have
recently started to make synthetic ropes.

The repeating units of four polymers used in their products are shown in the table
below.

polymer listed repeating unit type of


in order of polymerisation
decreasing
tensile
strength

O O

E C N CN

H H

O H

C 2H C 2H C 2 C C H H C 2H 2 N
F
C C 2H N C 2H C 2H C 2H C 2H

O H

O C 2H C
C 2H O
G
C

H C 3H

H C C

H H

(a) Complete the table by stating the type of polymerisation by which each polymer is
formed.
[2]

(b) Name the functional group joining the monomer units in polymer G.

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Bishop Thomas Grant School 19
[1]

Bishop Thomas Grant School 20


(c) Polymer H is used as a replacement for hemp, a natural fibre.

At the end of a rope’s useful life, it has to be disposed of.

Suggest one advantage that hemp has over polymer H in terms of the method of
disposal.

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[1]

(d) In this question, one mark is available for the quality of spelling, punctuation and
grammar.

A rope for a particular purpose needs to have a minimum tensile strength.

The order of the polymers’ strengths is shown in the table.

Discuss, in terms of the different types of intermolecular interactions, the reasons


for this order and why polymer E is by far the strongest polymer.

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[5]
Quality of Written Communication [1]

(e) (i) Give the reagent and conditions for hydrolysing polymer G.

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

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

Bishop Thomas Grant School 21


(ii) Draw the structural formulae of the two organic products formed from the
reaction in (i).

[2]

(f) In Arctic conditions many polymers become unsuitable for use as ropes.

Suggest and explain why.

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[3]
[Total 17 marks]

14. Rhodium and cobalt have many important catalytic uses. For example rhodium is an
important component of catalytic converters for car exhausts. Rhodium compounds are
used as homogeneous catalysts to make ethanoic acid from methanol.
8 1
(i) Rhodium atoms have an outer electron structure of 4d 5s .

Suggest two ways in which the outer electron structure for a cobalt atom is
different from the outer electron structure for a rhodium atom.

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[2]

Bishop Thomas Grant School 22


(ii) Explain why rhodium and cobalt are able to act as catalysts.

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[2]

(iii) What essential property must the rhodium compounds have to act as
homogeneous catalysts in the manufacture of ethanoic acid?

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[1]
[Total 5 marks]

15. Another way to measure the concentration of iron(III) ions in solution is to carry out a
titration.
The iron(III) ions are first reduced to iron(II) ions and then an acidified sample is titrated
with a standard potassium manganate(VII) solution.

The equation for the titration reaction is given below.


2+ – + 3+ 2+
5Fe (aq) + MnO4 (aq) + 8H (aq) → 5Fe + Mn (aq) + 4H2O(l)

(i) Name a suitable acid to acidify the sample.

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[1]

Bishop Thomas Grant School 23


3 –3 –
(ii) 25.0 cm of an iron(II) solution is titrated with a 0.0100 mol dm MnO4 solution.

3
The average titre is 16.60 cm .

Calculate the concentration of the iron(II) solution.

Give your answer to an appropriate number of significant figures.

–3
concentration = .......................................... mol dm
[3]

(iii) How can you tell when the titration reaches its end point?

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[1]
[Total 5 marks]

16. (a) Iron(III) ions are present in the stream as complex ions.

Complete the following table about these complex ions.

name of ligand in complex

coordination number of complex

name of shape of complex

[3]

Bishop Thomas Grant School 24


(b) As a result of the increased acidity of the stream water, other d-block metal ions
are leached into the water. Zinc(II) ions are often found in the water but are not
noticed because they are colourless.

What feature of d-block metal ions enables some to be coloured in solution?

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

(c) Very dilute solutions of iron(III) ions are almost colourless. Addition of potassium
thiocyanate leads to a deep red coloured complex.

(i) What type of reaction occurs?

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[1]

(ii) What technique would you use to determine the concentration of the
complex formed?

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[1]
[Total 6 marks]

17. A chemical peel is a solution used to improve and smooth the texture of facial skin by
removing its damaged outer layers. Jessener’s Peel contains compounds A, B and C,
whose structures are shown below.

O H O H O H

O
O

O H
O H O H
A B

Bishop Thomas Grant School 25


Compounds A, B and C can be identified using infrared spectroscopy. The infrared
spectrum of one of these compounds is shown below.

1 0 0
tr a n s m itta n c e ( % )

5 0

0
4 0 0 0 3 0 0 0 1 5 0 0 2 0 0 0 1 0 0 0
w a v e n u m– 1 b e r / c m

Identify the compound and provide two pieces of evidence from the spectrum to
support your answer.

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[Total 3 marks]

Bishop Thomas Grant School 26


18. The polymers neoprene and nylon-6 are waterproof, elastic and highly resistant to
abrasion. These properties make them suitable for the manufacture of outdoor
garments.

(a) Complete the table by drawing the structure of the monomer of neoprene and the
repeating unit for nylon-6.

polymer monomer repeating unit

C l

neoprene

2-chloro-1,3-butadiene

nylon-6 HOOC—(CH2)5—NH2

[2]

(b) In the polymer chains of neoprene, 90% of the double bonds are in a trans
arrangement.

(i) Explain why neoprene can form cis and trans isomers.

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[2]

(ii) Describe and explain the effect on the crystallinity of neoprene of changing
the composition of the double bonds to 50% of trans and 50% of cis.

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Bishop Thomas Grant School 27


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[2]

Bishop Thomas Grant School 28


(c) Materials made from nylon-6 can absorb moisture but those made from neoprene
cannot.

• Explain these observations.

• Describe the effect of water absorption on the chain arrangement in nylon-6


and thus on its glass transition temperature (Tg).

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[4]

(d) Nylon-6 is hydrolysed by heating under reflux with aqueous sodium hydroxide.

Draw the structural formula of the organic product of this reaction.

[2]
[Total 12 marks]

Bishop Thomas Grant School 29


19. It is thought that using virgin olive oil in cooking reduces the risk of cancer from free
radicals.

Chemists have shown that the oil contains tyrosol and hydroxytyrosol, which are strong
scavengers of free radicals.

A mixture of these two liquid compounds, tyrosol and hydroxytyrosol, is extracted from
olive oil.

Describe how you would carry out thin layer chromatography to show that there are two
compounds in a mixture.

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[Total 5 marks]

20. The water from wells in some rural areas smells of rotten eggs due to the presence of
hydrogen sulfide from decaying vegetable and animal matter. The smell can be
removed by the addition of dilute aqueous potassium manganate(VII).

(a) (i) Balance the equation below for the reaction removing the
‘rotten egg’ smell.
– +
........ H2S + ........ MnO4 + 2H → ........ MnO2 + ........ S + 4H2O
[1]

(ii) Give the oxidation state of Mn in MnO2.

oxidation state of Mn = .....................................


[1]

Bishop Thomas Grant School 30


(b) The potassium manganate(VII) will also remove any iron(II) ions, which are
often present in water from wells, converting them to Fe(III).

A student added some drops of potassium manganate(VII) solution to a sample


of water from a well containing iron(II) ions. He then added excess sodium
hydroxide solution and observed a red-brown precipitate.

(i) Name the precipitate.

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

(ii) Give the ionic equation for the formation of the precipitate. Include state
symbols.


[2]
[Total 5 marks]

21. Non-returnable drinks bottles are often made from PET. This produces a huge problem
for waste disposal. However, this polymer cannot be used to make returnable bottles.

(a) PET is a polyester. The repeating unit for PET is given below.

O O

C C O 2 C C H 2H O

Draw a ring around the ester group in the repeating unit above.
[1]

Bishop Thomas Grant School 31


(b) Plastic waste is often buried for disposal.

Give two other methods which are used to deal with plastic waste and explain a
different advantage for each method.

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[4]

(c) PET is not used to make returnable bottles because its glass transition
temperature, Tg, is too low.

Explain why lowering the temperature of PET below its Tg causes it to become
brittle.

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[3]
[Total 8 marks]

Bishop Thomas Grant School 32


22. Non-returnable drinks bottles are often made from PET. This produces a huge problem
for waste disposal. However, this polymer cannot be used to make returnable bottles.

(a) Chemists have developed a new polyester which can be used for producing
returnable bottles. It can be made from ethane-1,2-diol, HOCH2CH2OH, and
compound A. The structure of compound A is shown below. The polymer is
known as PEN.

C O O H

H O O C

c o m p o u n d A

(i) Draw the skeletal formula of the repeating unit of PEN.

[2]

(ii) PEN has a higher melting temperature than PET.

Assume both polymers have similar average relative molecular masses.

Suggest why PEN has a higher melting temperature than PET.

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[2]

Bishop Thomas Grant School 33


(iii) Explain how the infrared spectra of compound A and PEN would differ in
one significant respect. Use the Data Sheet to look up any relevant
absorbances you need.

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[2]

(b) Industrially, PEN is made by reacting a diester of compound A with ethane-1,2-


diol.

The diester is made by reacting compound A with ethanol according to the


equation below.

C O O H C O 2O C5 H
+ 22 H C 5 O H + 22 O H
H O O C C H O O C
2 5

c o m p o u n d A

(i) What other chemical is added to an acid and alcohol mixture and what
conditions are used to make an ester in the laboratory?

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[2]

(ii) Classify the reaction in which PEN is made by underlining one of the
following reaction types.

addition condensationelimination rearrangement


[1]

Bishop Thomas Grant School 34


(iii) Explain, using ideas of atom economy, why the polymerisation reactions in
which PET and PEN are formed are less environmentally friendly than
those in which poly(ethene) is made.

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[3]

(iv) Compound A and its diester can be distinguished by thin-layer


chromatography.

A spot of a mixture of the two is run on a TLC plate.

Draw a diagram of the resulting TLC plate showing the located spots.

Explain how you would measure the Rf values of the spots.

[2]
[Total 14 marks]

23. Groundwater usually contains iron compounds and therefore water from wells will
contain significant amounts of iron compounds. The main problem with household
water containing iron compounds is the staining it causes to laundry, porcelain and
plumbing fittings.

(a) Water containing iron in an oxidation state of +2 is known as ‘clear water’ since it
appears colourless. However, on leaving the tap it may become coloured and it is
then referred to as ‘red water’. ‘Red water’ contains iron(III) compounds.

(i) Give the formula of the complex ion which causes the ‘red’ colour.

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[1]

Bishop Thomas Grant School 35


(ii) What causes the colour change when clear water leaves the tap?

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[2]

(iii) If the ‘red water’ is made slightly alkaline, for example by adding sodium
hydroxide solution, a red–brown precipitate will form.

Write an ionic equation for the formation of the red–brown precipitate.

Include state symbols.

[3]

(b) ‘Iron stains’ contain iron(III) compounds and can be removed using a variety of
products available in the supermarket. One commonly used chemical is
ethanedioic acid. It is used in stain removers as the disodium salt.
2–
(i) Draw the full structural formula of the ethanedioate ion, C2O4 .

[1]

(ii) Name the type of reaction that occurs when ethanedioate ions in aqueous
3–
solution react with ‘red water’ to form green [Fe(C2O4)3] ions.

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[1]

Bishop Thomas Grant School 36


(iii) Explain why a green substance looks green.

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[2]
[Total 10 marks]

Bishop Thomas Grant School 37