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Marking Scheme

1- a) Lower temperature results in lower energy (1m)

Fewer effective collisions (1m)
Rate slower (1m)

b) Some reference to cost (1m)

Increased in yield does not justify cost of higher pressure (1m)

c) i) Increased rate (1m)

Provides an alternative route with a lower activation energy (1m)

ii) no effect (1m)

catalyst does not affect position of equilibrium / catalyst afffects
both reactions equally (1m)
TotalQ1 = 9 marks

2- i) Kc = (1m)

ii) 4HCl + O2 2Cl2 + 2H2O

0.8 mols 0.2 mols ___ ____

–4x –x + 2x + 2x
0.8 – 4 x 0.2 – x 2x 2x (1m)
0.8 – 4 x = 0.2 x = 0.150
no moles HCl = 0.200
no moles O2 = 0.050
no moles Cl2 = 0.300
no moles H2O = 0.300 (1m)

[HCl]eq = 0.020
[O2]eq = 0.005
[Cl2]eq = 0.030
[H2O]eq – 0.030 (1m)

Kc = 1010 or 1012 or 1013 or 1012.5 or 1.01 × 103 mol-1 dm3

( ½ m for answer and ½ m for units)

TotalQ2 = 5 marks
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3- a) Kp = (1m)

b) Let no moles N2O4 = 100 initially

N2O4 2NO2

100 _____
–x + 2x
20 ??
(1m)

100 – x = 20 x = 80

(1m)

(1m)

(1m) atm (1m)

c) i) Reaction is endothermic (1m)

Kp increases (1m)
Equilibrium position shifts to the right (1m)

ii) darker colour (1m)

TotalQ3 = 10 marks

4- a) [H+] = 0.074 mol dm-3

 [HCl] = 0.074 mol dm-3 (1m)

b) [H+] = 5.89 x 10-5 mol dm-3 (1m)

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 H +   OCl- 
Ka = (1m)
 HOCl
[H+] = [OCl-] (1m) or implied in calculation
2
 H+ 
[HOCl] =   = 0.0932 mol dm-3 (1m)
Ka
Total Q4= 5 marks

5- a) only partially dissociated (1m)

into H+ ions (1m)

 H 3O +   A - 
b) Ka = (1m)
 HA 
c) i) 9.8 to 10 (1m)

ii) 9.8 to 10 (1m)

iii) pKa = 5.8-6.0 (1m)

Ka = 1.58 × 10 – 1.0 × 10-6
-6
(1m)

d) i) Resists change in pH (1m)

on addition of small amounts of acid / base (1m)

ii) 5.8 to 6.2 (1m)

answer same as c) iii) (1m)
Total Q5= 11 marks

6- a) Starts at 22 (1m)
Vertical section at 40cm3 of NaOH (1m)
vertical section centered between pH 8 – 9
and between 2 to 3 pH units (1m)
Shape to include initial jump and finish between pH = 12 – 13 (1m)

b) i. If an acid is added:
HCOO-(aq) + H3O+(aq)  HCOOH(aq) + H2O(l)
If a base is added:
HCOOH(aq) + OH-(aq)  HCOO-(aq) + H2O(l)

 base
ii. pH = pKa + log (1m)
 acid 
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0.25
pH = - log(1.78 x 10-4) – log (1m)
0.125
pH = 3.4 (5) (1m)
TotalQ6 = 11 marks
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7-
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Total Q7= 7 marks

8-Two compounds, A and B, are isomers with molecular formula

C4H8O.

• Both compounds produce an orange-yellow precipitate with

2,4-
dinitrophenylhydrazine.

• Both compounds react with sodium borohydride (sodium

tetrahydridoborate(III)).

• When the compounds are warmed separately with Fehling’s

solution, A forms a
red-brown precipitate but B does not.

• Compound B forms yellow crystals when warmed with aqueous

iodine and
sodium hydroxide, whereas A does not.
(a) Draw full structural formulae for A and B, showing all
bonds.
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(b) Draw the structural formula of the product from the reaction
of compound A with2,4-dinitrophenylhydrazine.

(c) Give the name and formula of:

(i) The yellow solid formed when compound B reacts with

aqueous iodine and sodium hydroxide:
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(ii) The organic product of the reaction between compound B

and sodium
borohydride(sodium tetrahydridoborate(III)) in water:

(d) Molecules of the organic product formed in (c)(ii) are chiral

and exist as
optical isomers.

(i) What is meant by the term chiral molecule?

(It is not) superimposable on its mirror image

Or does not have a plane of symmetry
Or does not have a centre of symmetry (1)
(ii) How could the optical isomers of the compound formed in
(c)(ii) be distinguished from each other?

Rotate (the) plane (of plane ) polarised (monochromatic) light

(equally) in opposite directions (1)
OR
pass polarised light through sample
OR use a polarimeter
rotates the plane (equally) in opposite directions (1)
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Total Q8=10 m
9-a) Describe what you would see and write the equations for the reactions of
propanoic acid with:

(i) A solution of sodium carbonate

(2m)

(ii) Solid phosphorus pentachloride.

(2m)

b) Propanoic acid can also be prepared from propanal, CH3CH2CHO. State the
reagents for this conversion.

c) 1-aminobutan-2-ol, CH3CH2CH(OH)CH2NH2, is an active ingredient in some

deodorant sprays.

It can be prepared from propanal by the following two-step process.

(i) For Step 1

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State the reagents and conditions.

(2m)

Total Q9=9 m

10- In moths a pheromone, P, acts as an attractant for the opposite sex. P has the
molecular formula C7H12O.

What can be deduced about the structure of P from the following information?

(a) (i) 1 mole of P reacts with 1 mole of Br2 molecules to form a compound with
the formula C7H12OBr2.

Contains one carbon-carbon double bond

(1m)

(ii) When lithium tetrahydridoaluminate is reacted with P a compound with

the formula C7H14O is formed.

It is a carbonyl compound/ accept aldehyde or ketone/ carbonyl group

reduced

(1m)

(iii) P forms an orange precipitate with 2,4-dinitrophenylhydrazine.

It is an aldehyde or ketone (carbonyl compound)

(1m)

(iv) When P is heated with Fehling’s or Benedict’s solution, the solution

remains blue.

It is a ketone not aldehyde

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(1m)
(v) P is a Z-isomer.

Has two groups on the same side of a C=C / cis isomer

(1m)

(b) What does the following physical data tell you about the structure of P? Use
the Data booklet attached where necessary.

(i) The infrared spectrum of P has the following absorptions at wave

numbers above
1600 cm–1.

3060 cm–1 alkene (C-H stretching)

2920 cm–1 alkane (C-H stretching)
1690 cm–1 ketone (C=O stretching)
1660 cm–1 alkene (C=C stretching)

4 correct à 3 marks
3 correct à2 marks
2 correct à 1 mark

(ii) The nmr spectrum does not have a peak corresponding to a chemical shift,
δ, of between 9 and 10.

Not an aldehyde
(1m)

(iii) The mass spectrum showed the presence of peaks at mass/charge ratios
of 15 and 29, but no peak at 43.

15 : CH3 group (1m)

29: C2H5 group (1m)
43: no C3H7 group (1m)

(c) Given that P has a straight chain of carbon atoms in its formula, use the
information you have deduced above to suggest a displayed formula for the
pheromone P.

C2H5 – C = C – CH2COCH3
H H
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(2m)

(d) How could you use a purified sample of the orange precipitate in (a)(iii) to
confirm the formula of P?

Measure its melting temperature (1m)

And compare with data book values (1m)

Total Q10=16 m

11- Terylene is a polymer made from ethane 1,2-diol and benzene- 1,4-
dicarboxylic acid. It is a condensation polymer.
(a) Draw the structural formulae of the two compounds which are used to
make Terylene.

HOCH2CH2OH (1)

(b) Give a structural formula for the polymer.

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(2m)

(c) Explain the meaning of the term condensation in this context.

2 molecules joined together by loss of water (1)

(d) Suggest why polyesters are not suitable for use under strongly alkaline
conditions.

hydrolyses (easily) / saponification (1)

Total Q11=6 m

12- The following procedure can be used to prepare ethyl

ethanoate (boiling temperature 77°C).

• Mix 20 cm3 of ethanol (an excess) and 12.6 g of ethanoic acid in a

pear-shaped
flask.
• Slowly add 8 cm3 of concentrated sulphuric acid, with cooling and
mixing.
• Heat the mixture under reflux for 15 minutes.
• Allow the apparatus to cool and then re-arrange it for distillation.
• Collect everything that distils up to 80°C.
• Purify the distillate.

(a) Write the equation for the reaction between ethanol and
ethanoic acid.

CH3COOH + C2H5OH  CH3COOC2H5 + H2O (1)

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(b) What is the purpose of the concentrated sulphuric acid in this

reaction?

Catalyst/ speeds up reaction (1)

(c) Draw a diagram to show how you should set up the apparatus to
distil the mixture.

Flask with still head (1)

Condenser and a receiver (1)
Thermometer at the correct place (1)
Drawing in pencil (1)

(d) 10.6 g of pure ethyl ethanoate was collected.

Calculate the percentage yield of ethyl ethanoate obtained in
this experiment.

Moles ethanoic acid = 12.6/60 = 0.21 (1)

(Moles of ethyl ethanoate = 0.21)
Theoretical mass of ethyl ethanoate = 0.21 × 88 = 18.48
g (1)
% yield = (10.60/18.48) × 100 = 57 (1)

(e) Ethyl ethanoate can also be prepared from ethanol and ethanoyl
chloride.

(i) Write the equation for this reaction.

C2H5OH + CH3COCl  CH3COOC2H5 + HCl (1)

(ii) Explain why the yield obtained by this method is

significantly higher than that from ethanoic acid.

Reaction with ethanoic acid reaches equilibrium or

reaction with
ethanoyl chloride goes to completion. (1)

(TotalQ12= 12 marks)
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13-(a) Primary alcohols can be oxidised to aldehydes. The following are the
instructions for the oxidation of ethanol (boiling temperature 78 ºC) to
ethanal (boiling temperature 21 ºC).

· Place 50 cm3 of water in a round bottom flask and add, carefully with
stirring, 17 cm3 of concentrated sulphuric acid. Arrange the flask, with a tap
funnel attached, in a distillation apparatus.

· Dissolve 50 g of sodium dichromate(VI) in 50 cm3 of water and add 40 cm3 of

ethanol, mix and place in the tap funnel.

· Heat the dilute acid in the flask until it is boiling and then remove the flame.

· Slowly run the solution of sodium dichromate(VI) into the flask. A vigorous
reaction takes place.

· Collect the mixture of ethanal and water, which distils off, in a conical flask,
which is surrounded by iced water.

(i) Draw a diagram of the apparatus which could be used for this reaction.

Flask + tap funnel (1)

Stillhead + condenser (1)
Receiving conical flask in ice (1)

(ii) Explain why the ethanol and the oxidising agent are not initially placed in
the round-bottomed flask with the sulphuric acid.

To prevent further oxidation (to carboxylic acid )/ to stop at aldehyde

(1m)

(iii) Explain why the heat is removed before the solution of ethanol and
sodium
dichromate(VI) is added.

Reaction is exothermic / heat given out in reaction

(1m)

(iv) Suggest why the flask in which the product is collected is surrounded by
iced water.
 Page 16 of 43

Ethanal has low b.temp / has high v.p. at room temp is / volatile / to
prevent evaporation of ethanal

(1m)

b) Butanone can be made from 2-bromobutane by a synthetic route involving two

steps, the first using aqueous sodium hydroxide and the second potassium
dichromate(VI) solution acidified with dilute sulphuric acid.

Give the structural formula of the intermediate compound in this synthetic

route.

(1m)
(TotalQ13= 7 marks)

14- Compound V the structure of which is shown below, is found in human sweat.
 Page 17 of 43

a) Compound V has two functional groups. Identify both functional groups and state
a chemical test for each. The result of each chemical test should be included in
your answer.

1st functional group C=C (alkene) (1)

Test with bromine water , orange/brown turns colourless. (1)
2nd functional group carboxyl group (carboxylic acid) (1)
Test could be add sodium carbonate or hydrogencarbonate fizzing occurs (1)

b) Compound V can be converted into two carbonyl compounds, W and X shown

below:

i) Which of the compounds, W or X would react when warmed with Fehling’s

solution? Justify
your answer.

W as it has an aldehyde group (1)

ii) Compound W can be reduced in two steps to compound Y of molecular

formula C2H6O2.

Identify Y:

CH2OHCH2OH (1)

iii) Compound W can be oxidized to compound Z of molecular formula C2H2O4.

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Identify Z:

HOOCCOOH (1)

c) The compound Y and Z react together under certain conditions to form a polymer.

i) Draw the structural formula of the repeating unit for the polymer formed

ii) What type of polymerization reaction occurs between compounds Y and Z?

Condensation (1)

(TotalQ14= 10 marks)

15-This question concerns the compounds in the following reaction scheme:

 Page 19 of 43

(a) F and G are compounds which both decolorise bromine water. F has two
stereoisomers.

(i) What functional group is present in both F and G?

>C=C< / carbon–carbon double bond / alkene (1)

(ii) Give the structural formulae of both stereoisomers of F.

 Page 20 of 43

(iii) Explain how these two isomers arise.

no/restricted rotation about C=C bond (1)

some reference to the relevance of p bonds or overlapping p–orbitals/
substit groups on each carbon atom not the same (1)

(iv) Write the structural formula of G.

CH3CH2CH=CH2 (1) accept C2H5CH=CH2

(b) B cannot be oxidised by acidified potassium dichromate(VI) solution.

(i) Write the structural formula of B.

(ii) Draw the general structural features of molecules which can be detected
by the reaction with iodine and alkali.

(iii) Give the structure of the substance in solution D, and of the product E.

(c) The mass spectrum of A gives peaks at m/e 29 and 45, amongst others.
That at 45 is the largest. This spectrum shows no molecular ion peak,
which would be expected at m/e 74. A is chiral.

(i) Give the structural formula for A.

(1)
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(ii) Identify the ions responsible for the peaks at m/e 45 and 29, and hence
suggest why the molecule shows no molecular ion peak.

(TotalQ15= 15 marks)

16- a. (i) Parts of the side chains break off. Compound A will form an ion
due to CH2OH at m/z = 31; compound B will form an ion at 29
due to CH2CH3. (1m)
This peak is not present in the spectrum. (1m)

(1m)

b. The peak between 3230 cm−1 and 3550 cm−1 is due to the hydrogen
bonding in alcohols (1m) and therefore the spectrum is for compound A.
(1m)

(TotalQ16= 5 marks)
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17-
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(TotalQ17= 12 marks)

18-
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Total Q18=11 marks

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19-

Total Q19= 8marks

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20-
 Page 28 of 43

(Total for Question 20= 9 marks)

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21-

Total Q21=13 marks

22-a)(i) Number of protons (in the nucleus) (1)

 Page 30 of 43

(1 mark)
59 60 60
(ii) Co has 32 neutrons but Co has 33 neutrons / the Co has one more
neutron than the 59Co (1)
(1 mark)
(iii) Both have the same number of (outer) electrons/ both have same
electronic structure / chemical reaction involves electrons (Must have
some reference to electrons)
(1 mark)
(b)

(2 marks)
(c) (i) Electronic configuration differs from previous element by an electron in
a d(sub) shell / d-shell is filling (1)
(1 mark)
(ii) Forms ions or compounds with partially full/incomplete d sub shell (1)
(1 mark)
(d) (i) Lone pair / non bonding pair (of electrons) (1)
(1 mark)
(ii) Dative/ co-ordinate (1)
covalent (1)
(2 marks)
(iii) Octahedral or correct 3D diagram (1)
(1 mark)
(e) (i) Cobalt (II) hydroxide (1)
A name based on tetraaquodihydroxo cobalt (II) could score the mark.
[Co(H2O)6]2+ + 2OH-  Co(OH)2 + 6H2O
[Co(H2O)6]2+ + 2OH-  Co(OH)2(H2O)4 + 2H2O
[Co(H2O)6]2+ + 2NH3  Co(H2O)4 (OH)2 + 2NH4+
[Co(H2O)6]2+ + 2NH3  Co(OH)2 + 2NH4+ + 4H2O (1)
(2 marks)
(ii) Deprotonation / acid – base (1)
(1 mark)
2- 2- 4-
(iii) [Co(OH)4] / [Co(OH)4. (H2O)2] / [Co(OH)6] /[Co(OH)2. (H2O)4 ]
[Co(OH)3(H2O)3]-/ [Co(OH)5(H2O)]3-(1)
(1 mark)
(iv) [Co(H2O)6]2+ + 4Cl-  [CoCl4]2- + 6H2O (1)
Ligand exchange / Ligand substitution /Ligand replacement / Ligand
displacement (1)
(2 marks)
(TotalQ22= 17 marks)

23- (a) (i)

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(2 marks)
(ii) 3d54s1 (1) increased symmetry / stability of 3d if half-full (1)
(2 marks)
x 2- 2
(b) (i) (+6) (1) calculation based on [Mn (O )4] (1)
(2 marks)
(ii) Forms ion with octet (1) which is most favorable of the configurations
available (1)
(2 marks)
(iii) ionisation energies rise comparatively slowly (1) and higher ones are
offset by lattice / hydration / bond energies (1)
(2 marks)
(c) (i)

(4 marks)
(ii) the catalysed reaction is between oppositely charged ions rather
than similarly charged ions in the uncatalysed (1) (not lower Ea
unless stated for both reactions)
(1 mark)
(iii) variable oxidation state (1)
(1 mark)
(TotalQ23= 16 marks)

24- (a) Electron loss

(1 mark)
(b) Coloured ions / compounds (NOT metals) (1) complex ions / form
complexes (1) paramagnetic ions / compounds (1) variable valency or
oxidation state(1) catalytic activity (1) high melting or boiling
temperature / high density (1) ; NOT part filled d- shells or jus
‘paramagnetism’
(3 marks)
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(c)

(numbers of electrons acceptable)

half filled d (sub-) shell / orbital in Fe3+ /paired electrons in Fe2+(1)
(3 marks)
(d) (i) A to B deprotonation (1)
B to C ligand exchange / transfer / complex(ion) formation (1)
(2 marks)
(ii) Cu(OH)2 (1) accept up to four water molecules in addition
(1 mark)
(iii) [Cu(NH3)4]2+ (1) planar drawn (1); NOT tetrahedral
OR [Cu(NH3)4 (H2O)2]2+ (1) octahedral drawn (1)
OR [Cu(NH3)6]2+ (1) octahedral drawn (1)
Allow any of 1 to 6 (NH3) with 5 to 0 (H2O) to balance
(2 marks)

(e) (i) Cu2+ + 2l   Cul + ½l2 (1) or doubled; state symbols not required
(1 mark)
2- - 2-
(ii) I2(aq)+2S2O3 (aq)→2I (aq)+S4O6 (aq)

mol Cu = 0.6  2 / 63.5 = 0.0189 mol S2O32- (1)

0.0189mol
 vol = = 18.9 OR 19 cm3 (1)
1 mol dm  3
mark consequentially on equation in (1)
(3 marks)
(TotalQ24= 16 marks)
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25-
 Page 34 of 43

(Total for Question 25= 10 marks)

 Page 35 of 43

26-
a The reagents are concentrated nitric acid 1m and concentrated sulfuric acid. 1m
The conditions are heat to 50C 1m
At a higher temperature some dinitrobenzene will be produced and at a
lower temperature the reaction will be too slow. 1m
The equation is:

1m

1m for each reaction, 1m for correct use of curly arrows

1m
(ii) The lone pair of electrons (the 2pz electrons) on the oxygen atom in
phenol becomes partly delocalized into the benzene ring -bond. 1m This
increases the electron density in the ring and makes it more susceptible to
electrophilic attack, 1m and so has a lower activation energy, making the
reaction faster. 1m

Total Q26=13 marks

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27-
 Page 37 of 43

(Total for Question 27 = 9 marks)

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28-
 Page 39 of 43

Total for Question 28= 8 marks

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29-
 Page 41 of 43

(Total for Question 27 = 12 marks)

 Page 42 of 43

30- This question concerns the three isomers A, B and C, each of which has a
relative molecular mass of 134.

(a) The mass spectrum of substance A is shown below. Identify the species
responsible for the peaks labelled 1, 2 and 3.

(b) The infra-red spectra of two of these substances were also measured.

(i) Use the table and the spectra below to identify which spectrum is that of
substance C.
 Page 43 of 43

The spectrum of substance C is spectrum number

IR spectrum number 2 (1)

(ii) Give one reason for your choice.

(1)
(iii) Give one other reason why the other spectrum could not be that of
substance C.

The other has a peak at approx. 1700 cm–1 caused by

C=O
(1)
Total for Question 30=6 marks)