Mark Scheme (Results)

October 2021

Pearson Edexcel International Advanced Level

In Chemistry (WCH15)
Paper 01:Transition Metals and Organic
Nitrogen Chemistry
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October 2021
Question Paper Log Number P67131A
Publications Code WCH15_01_2110_MS
All the material in this publication is copyright
© Pearson Education Ltd 2021
General Marking Guidance

 All candidates must receive the same treatment. Examiners

must mark the first candidate in exactly the same way as
they mark the last.
 Mark schemes should be applied positively. Candidates must
be rewarded for what they have shown they can do rather
than penalised for omissions.
 Examiners should mark according to the mark scheme not
according to their perception of where the grade boundaries
may lie.
 There is no ceiling on achievement. All marks on the mark
scheme should be used appropriately.
 All the marks on the mark scheme are designed to be
awarded. Examiners should always award full marks if
deserved, i.e. if the answer matches the mark
scheme. Examiners should also be prepared to award zero
marks if the candidate’s response is not worthy of credit
according to the mark scheme.
 Where some judgement is required, mark schemes will
provide the principles by which marks will be awarded and
exemplification may be limited.
 When examiners are in doubt regarding the application of
the mark scheme to a candidate’s response, the team leader
must be consulted.
 Crossed out work should be marked UNLESS the candidate
has replaced it with an alternative response.
Section A (Multiple Choice)

Question Answer Mark

number
1(a) 1
The only correct answer is D (Pt, Pt)

A is incorrect because both electrodes should be made of platinum

B is incorrect because both electrodes should be made of platinum
C is incorrect because both electrodes should be made of platinum

Question Answer Mark

number
1(b) 1
The only correct answer is C (1.00 mol dm3 HCl(aq))

A is incorrect because H3PO4 is not completely ionised

B is incorrect because H2SO4 is not completely ionised
D is incorrect because CH3COOH is not completely ionised

Question Answer Mark

number
1(c) 1
The only correct answer is B (17.91 g)

A is incorrect because there should be only one mol of chromium ions per mol of dichromate ions
C is incorrect because there should be only one mol of chromium ions per mol of dichromate ions
D is incorrect because there should be only one mol of chromium ions per mol of dichromate ions
Question Answer Mark
number
1(d) 1
The only correct answer is A (H2SO4)

B is incorrect because chloride ions could be oxidised

C is incorrect because bromide ions would be oxidised
D is incorrect because this would introduce additional chromium species into the mixture

Question Answer Mark

number
2 1
The only correct answer is C (Pt Fe2+, Fe3+ ∥ [MnO4 + 8H+], [Mn2+ + 4H2O] Pt)

A is incorrect because both electrodes should be made of platinum

B is incorrect because both electrodes should be made of platinum and the MnO4/ Mn2+ half-cell does not show
reduction
D is incorrect because the MnO4/ Mn2+ half-cell does not show reduction

Question Answer Mark

number
3 1
The only correct answer is D (2Ag2+  Ag+ + Ag3+)

A is incorrect because the disproportionation is not thermodynamically feasible

B is incorrect because the disproportionation is not thermodynamically feasible
C is incorrect because the disproportionation is not thermodynamically feasible
Question Answer Mark
number
4 1
The only correct answer is A (the cathode has a more positive potential than the anode)

B is incorrect because oxidation always occurs at the anode

C is incorrect because oxygen is reduced at the positive electrode
D is incorrect because the overall reaction is the same under both acidic and alkaline conditions

Question Answer Mark

number
5 1
The only correct answer is B (carbon monoxide forms stronger dative covalent bonds with haemoglobin than does
oxygen)

A is incorrect because carbon monoxide can be displaced from carboxyhaemoglobin

C is incorrect because the formation of carboxyhaemoglobin does not lead to an increase in the entropy of the system
D is incorrect because the difference in bond type does not fully explain the difference in dative covalent bond strength

Question Answer Mark

number
6 1
The only correct answer is D (pink solution  blue precipitate  yellow-brown solution)

A is incorrect because CoCl2(aq) is a pink solution

B is incorrect because the blue precipitate dissolves in excess aqueous ammonia to form a yellow-brown solution
C is incorrect because CoCl2(aq) is a pink solution
Question Answer Mark
number
7 1
The only correct answer is B ([Ni(EDTA)]2)

A is incorrect because chloride ions act as monodentate ligands

C is incorrect because ethanedioate ions act as bidentate ligands
D is incorrect because 1,2-diaminoethane molecules act as bidentate ligands

Question Answer Mark

number
8 1
The only correct answer is D (none of the products are harmful to the environment)

A is incorrect because the reactions occurring in catalytic converters involve heterogeneous catalysis
B is incorrect because carbon monoxide is adsorbed onto the surface of the catalyst
C is incorrect because nitrogen is desorbed from the surface of the catalyst

Question Answer Mark

number
9 1
The only correct answer is C (Mn2+)

A is incorrect because MnO4 ions are neither a product nor a catalyst in this reaction
B is incorrect because H+ ions are neither a product nor a catalyst in this reaction
D is incorrect because CO2 is not a catalyst in this reaction
Question Answer Mark
number
10 1
The only correct answer is A (both Fe2+(aq) and Fe3+(aq) catalyse the reaction)

B is incorrect because both Fe2+(aq) and Fe3+(aq) catalyse the reaction

C is incorrect because both Fe2+(aq) and Fe3+(aq) catalyse the reaction
D is incorrect because both Fe2+(aq) and Fe3+(aq) catalyse the reaction

Question Answer Mark

number
11 1

The only correct answer is D ( )

A is incorrect because this product is formed by the substitution of one chlorine atom in CHCl3
B is incorrect because this product is formed by the substitution of two chlorine atoms in CHCl3
C is incorrect because this product is formed by the substitution of all three chlorine atoms in CHCl3
Question Answer Mark
number
12 1
The only correct answer is C (330.7)

A is incorrect because this is the molar mass of bromobenzene

B is incorrect because this is the molar mass of the monosubstituted product
D is incorrect because this is the molar mass of the fully substituted product

Question Answer Mark

number
13 1
The only correct answer is C (CH3CH2CH2NH2 > NH3 > C6H5NH2)

A is incorrect because C6H5NH2 is the weakest base in the sequence

B is incorrect because CH3CH2CH2NH2 is a stronger base than NH3
D is incorrect because this shows the order of increasing basicity

Question Answer Mark

number
14 1

The only correct answer is B ( )

A is incorrect because this amine could be prepared by the reduction of butanenitrile

C is incorrect because this amine could be prepared by the reduction of 2-methylpropanenitrile
D is incorrect because this amine could be prepared by the reduction of 2,2-dimethylpropanenitrile
Question Answer Mark
number
15 1
The only correct answer is B (4)

A is incorrect because the repeat unit of the polymer is formed from four different amino acids
C is incorrect because the repeat unit of the polymer is formed from four different amino acids
D is incorrect because the repeat unit of the polymer is formed from four different amino acids

Question Answer Mark

number
16 1
The only correct answer is D (carbon dioxide giving carboxylic acids )

A is incorrect because Grignard reagents react with water giving alkanes

B is incorrect because Grignard reagents react with methanal giving primary alcohols
C is incorrect because Grignard reagents react with ketones giving tertiary alcohols only

Question Answer Mark

number
17 1
The only correct answer is C (will be lower than the true value)

A is incorrect because using a sample that is impure would cause the value to be lower
B is incorrect because using a sample that is impure would cause the value to be lower
D is incorrect because using a sample that is impure would cause the value to be lower
Total for Section A = 20 marks
Section B

Question
Answer Additional guidance Mark
Number
18(a) Example of calculation: 2

 any indication that A contains FeCl2/iron(II) chloride (1) Ignore (A contains) Fe2+
Ignore [FeCl4]2

 working to show that A is a tetrahydrate (1) mass of water = 198.8  (55.8 + 2  35.5)
= 72.0 (g)
moles of water = 72.0 ÷ 18.0 = 4

A is FeCl2.4H2O/iron(II) chloride tetrahydrate

Allow FeCl2(H2O)4

Question
Answer Additional guidance Mark
Number
18(b)  [Fe(H2O)6]2+ Allow [Fe(OH)(H2O)5]+ / [Fe(Cl)(H2O)5]+ 1

Ignore omission of square brackets

Ignore name even if incorrect
Question
Answer Additional guidance Mark
Number
18(c) Example of diagram: 1

 A diagram showing the octahedral shape

Accept arrows for dative covalent bonds

Allow CN for C≡N

Do not award KCN/HCN for C≡N
Do not award M for Fe

Ignore connectivity of CN ligands

Ignore lone pairs
Ignore omission of square brackets
Ignore all charges

Do not award diagrams with no 3D shape

Question
Answer Additional guidance Mark
Number
18(d) Example of calculation: 3

 moles of K, Fe (1) mol K = 35.6 ÷ 39.1 = 0.91049

Allow 0.91282 from Ar value of 39

mol Fe = 17.0 ÷ 55.8 = 0.30466

Allow 0.30357 from Ar value of 56

Ignore SF

 moles of C and N (1) mol C = 21.9 ÷ 12.0 = 1.8250

mol N = 25.5 ÷ 14.0 = 1.8214

Ignore SF except 1 SF

 calculation of K:Fe:C:N mole ratio K : Fe : C : N

and 0.91049 : 0.30466 : 1.825 : 1.8214
empirical formula (1) 3 : 1 : 6 : 6
empirical formula is K3FeC6N6
Allow K3Fe(CN)6
Allow elements in any order
TE on moles of K, Fe, C and N provided empirical formula is
closest whole number ratio

Correct answer with no working scores (3)

Question
Answer Additional guidance Mark
Number
18(e) An equation including: Example of equation: 2

2[Fe(CN)6]4 + Cl2  2[Fe(CN)6]3 + 2Cl

 [Fe(CN)6]4 reactant and [Fe(CN)6]3 product (1) Allow K4[Fe(CN)6] reactant and K3[Fe(CN)6] product
Ignore omission of square brackets

 rest of equation and balancing (1) M2 dependent on M1

Allow multiples
Ignore state symbols even if incorrect
Do not award uncancelled K+ spectator ions

If no other mark awarded, award (1) for any multiple of the

following equation:
2Fe2+ + Cl2  2Fe3+ + 2Cl

Question
Answer Additional guidance Mark
Number
18(f) A completed table showing: Example of completed table: 2

 correct identification for reaction 2 (1)

 correct identification for reaction 3 (1)

Allow any form of positive identification, including crosses

Ignore any form of negative identification

Do not award more than 1 box ticked in each row

(Total for Question 18 = 11 marks)
Question
Answer Additional guidance Mark
Number
19(a)  suitable test: bromine water/Br2(aq) (1) Allow bromine / Br2((l)) / Br2 in organic solvent 2
Do not award Br/Br

Accept potassium manganate((VII))/KMnO4 and acidified/

named acid/H+

Do not award hydrogenation

Do not award combustion

 result of test: decolourises (from orange) with Allow does not decolourise with benzene
Dewar structure (and no change with benzene) (1) Allow brown/orange/yellow for colour of bromine water
Allow red/brown/orange for colour of bromine
Allow pink/purple for colour of potassium manganate((VII))

Ignore colour fades for decolourises

Ignore reference to addition/substitution

Do not award any reference to decolourisation/reaction with

benzene
Question
Answer Additional guidance Mark
Number
19(b) Ignore any reference to IR and/or 13C NMR 2

 similarity: (both compounds have) one (NMR) peak (1) Allow (both compounds have) one proton environment
Ignore just same number of peaks

Ignore references to relative peak area/integration/splitting

Do not award any other number of peaks

 difference: expected chemical shift values (1) chemical shift for benzene within range of 6.4 to 8.4 ppm
(actual value is 7.3 ppm)
and
chemical shift for Ladenburg structure within range of
0 to 2.3 ppm (actual value is 2.3 ppm)

Allow any range or value within the above ranges

Ignore just benzene would have a higher chemical shift than

Ladenburg structure or reverse argument

Do not award additional incorrect chemical shifts

Question
Answer Additional guidance Mark
Number
19(c) An explanation that makes reference to the following Ignore any reference to: 2
points: CH bonds
bond strength/bond angle
delocalised electrons
Dewar/Ladenburg structures

 showed that all CC bonds are the same length in Allow showed benzene is a regular hexagon
benzene (1)
Allow showed benzene contains only one type of
carbon-carbon bond

Allow benzene bond lengths are in between C=C and CC

Ignore just benzene has no C=C bonds

Do not award benzene bond lengths are longer than CC/

shorter than C=C

 in Kekulé structure the C=C bonds would be Allow Kekulé structure would have shown two different
shorter than the CC bonds (or reverse argument) (1) lengths/types of carbon-carbon bond

Allow Kekulé structure would have alternating carbon-carbon

bond lengths

Ignore just Kekulé has C=C bonds

Do not award CC bonds would be shorter than the C=C bonds

If no other mark awarded, just bond lengths equal in benzene

but different in Kekulé scores (1)
Question
Answer Additional guidance Mark
Number
19(d)(i) A diagram showing: Example of diagram: 2

 correct relative stabilities (1)

 two or three numerical differences in enthalpy

with appropriate arrows (1)

Allow names for structures

If three values and arrows are given they must all be correct to
score M2

Allow slight imprecision in start and end of arrows in M2

Ignore any x-axis label

Do not award double headed arrows in M2

Do not award incorrect sign in M2
Question
Answer Additional guidance Mark
Number
19(d)(ii) An answer that makes reference to the following: 1

 pi bonds are weaker/more reactive/require less Ignore just Dewar structure has pi/double bonds/is unsaturated
energy to break (than sigma bonds) Ignore just Dewar structure has weaker bonds
Do not award C=C/double bonds weaker/require less energy to
or break (than CC/single bonds)

fewer bonds must break to convert the Accept reverse argument

Dewar structure to benzene Allow any specified numbers to indicate fewer bonds must break

Ignore fewer new bonds must form

Ignore Dewar structure is more similar to benzene
Ignore carbon atoms already in a ring/hexagon
Ignore any reference to intermolecular forces

Do not award (higher) ring strain in Ladenburg

Do not award smaller difference in enthalpy
Do not award Ladenburg structure more stable
Question
Answer Additional guidance Mark
Number
19(e) An explanation that makes reference to the following Allow double bond for C=C throughout 2
points:

E-hexa-1,4-diene
 twice the hydrogenation enthalpy (of hex-3-ene) Accept 118  2 (=236) as two C=C bonds
as two (isolated) C=C bonds (1) Allow twice the hydrogenation enthalpy as no delocalisation of
pi-bond(s)

E-hexa-1,3-diene
 less exothermic/more stable (by 22 kJ mol1 than Accept less negative
E-hexa-1,4-diene Allow more positive
and
as some delocalisation of pi-bond(s) (1) Allow some delocalisation of double bond(s)
Allow double bonds/p-orbitals are conjugated
Allow double bonds/p-orbitals are close enough to overlap

Ignore just C=C are close

Ignore just delocalisation of electrons
Ignore electron density more spread out
Ignore resonance stabilised
Question
Answer Additional guidance Mark
Number
19(f)(i) Example of correct skeletal formulae: 2

 skeletal formula of any one isomer (1)

 skeletal formulae of second and third isomers (1)

(1,2-isomer) (1,3-isomer) (1,4-isomer)

Allow Kekulé benzene ring

Allow structural/displayed CH3 and CH3CO groups

If no other mark awarded, 1,2-, 1,3- and 1,4-isomers with

incorrect side chain/cyclohexane ring scores (1)

Question
Answer Additional guidance Mark
Number
19(f)(ii)  (identification of X as) 1,4-isomer (1) Allow any form of identification, including (f)(i) annotation 2
Allow just ‘1,4’ or ‘para’

 (7 peaks consistent with) 7 carbon environments (1) M2 dependent on a structure containing 7 carbon
environments

Accept 1,2-isomer and/or 1,3-isomer have 9 carbon

environments/would have 9 peaks

Allow (4 arene peaks consistent with) 4 arene carbon

environments

Allow 1,2-isomer and/or 1,3-isomer have 6 arene carbon

environments/would have 6 arene peaks
Question
Answer Additional guidance Mark
Number
19(f)(iii) A mechanism including: Example of mechanism: 4

Allow Kekulé benzene ring

 curly arrow from on or within circle
to C+ of CH3CO+ (1)

 structure of intermediate ion (1) ‘Horseshoe’ facing tetrahedral carbon and covering at least three
carbons with some part of positive sign within ‘horseshoe’

Allow methyl at 1,2- or 1,3-positions

Ignore missing methyl substituent

Do not award dotted/dashed CH/CC bonds unless 3D structure

 curly arrow from CH bond to within ring

and Allow 1,2- or 1,3-product from corresponding intermediate
correct product (1) Do not award missing methyl substituent

 balanced equation for regeneration of catalyst (1) AlCl4 + H+  AlCl3 + HCl

(Total for Question 19 = 19 marks)
Question
Answer Additional guidance Mark
Number
20(a) An answer that makes reference to one of the Ignore references to ionisation energy 1
following points: Ignore partially full d orbital(s)/d subshell
Ignore more than one stable ion
Ignore references to heterogeneous catalysis/adsorption
Ignore references to alternative reaction pathways/activation energy

 variable oxidation state/oxidation number Allow can change oxidation state/oxidation number
or Allow have different oxidation state(s)/oxidation number(s)
 (easily) oxidised and reduced (back to Ignore variable valency
original oxidation state)
or
 (easily) donate and accept electrons Allow just lose and gain electrons (easily)
(from other molecules/species)

Question
Answer Additional guidance Mark
Number
20(b)(i) An answer that makes reference to the following points: Accept coordinate for dative throughout 2

 monodentate: forms a single/one dative (covalent) bond (1) Accept donates a single/one lone pair
Allow occupies a single/one coordination site

 ligand: (a species with a) lone pair (of electrons) that can form
a dative (covalent) bond to a (central transition) metal (ion) (1)
Question
Answer Additional guidance Mark
Number
20(b)(ii) A completed diagram showing: Expected diagram: 1

 three adjacent THF/Cl ligands

Ignore lone pairs

Ignore 1 charge on Cl ligands

Question
Answer Additional guidance Mark
Number
20(c)(i)  yellow to (permanent pale) green Ignore qualifiers, eg pale 1
Ignore precipitate

Do not award green to yellow

Do not award any combination of yellow and green, eg yellowy-green
Do not award any other colour
Question
Answer Additional guidance Mark
Number
20(c)(ii) A calculation including: Example of calculation: 5

 moles of Ti3+ in titre (1) moles of Ti3+ = 0.085  20.70 = 0.0017595 / 1.7595  103
1000

 moles of Mg(NO3)2.6H2O in 100 cm3 (1) moles of Mg(NO3)2.6H2O = 0.75 = 0.0029263 / 2.9263  103
256.3

 moles of NO3 in 10.00 cm3 (1) moles of NO3 = 0.0029263  2 = 0.00058525 / 5.8525  104
10
TE on moles Mg(NO3)2.6H2O

Ignore SF except 1 SF in M1, M2 and M3

Ignore truncation of moles in M1, M2 and M3, eg 0.0005852

 Ti3+ : NO3 mol ratio (1) Ti3+ : NO3 mol ratio = 0.0017595 : 0.00058525
= 3 : 1
3+ 
TE on moles Ti and moles NO3

 final oxidation state of nitrogen (1) final oxidation state of nitrogen = (+)2

TE on mol ratio provided final oxidation state of nitrogen is

between 3 and +4, eg
Ti3+ : NO3 mol ratio = 0.0017595 : 0.00029263
= 6 : 1
final oxidation state of nitrogen = 1

Do not award incorrect oxidation state of N in NO3

Correct answer with no working scores (1)

Question
Answer Additional guidance Mark
Number
20(c)(iii) An equation including: Example of equation: 2
3Ti3+ + H2O + NO3  3TiO2+ + 2H+ + NO

 selection of correct nitrogen half-equation (1) TE on (c)(ii) provided +3 or +4 oxidation state

 balanced ionic equation from chosen half-equations (1) Allow multiples

Allow reversible arrow
Ignore state symbols even if incorrect

Question
Answer Additional guidance Mark
Number
20(c)(iv) An answer that makes reference to the following point: Example of calculation: 1

 (calculation of) Eocell value (Eocell = 0.96  0.10 =) (+)0.86 (V)

TE on ionic equation from (c)(iii):

(+)0.7(0) (V) for Ti3+ + NO3  TiO2+ + NO2
(+)0.84 (V) for 2Ti3+ + H2O + NO3  2TiO2+ + H+ + HNO2

Question
Answer Additional guidance Mark
Number
20(c)(v) An answer that makes reference to the following point: 1

 (heat is to) speed up/increase rate of reaction Allow to ensure fast oxidation of Ti3+
Allow to provide activation energy/Ea
Allow (reaction has a) high activation energy/Ea

Ignore just to provide (more) energy

Ignore to increase collision frequency
Ignore to ensure complete reaction
Ignore any reference to thermodynamic feasibility
Question
Answer Additional guidance Mark
Number
20(c)(vi) This question assesses a student’s ability to show a coherent and 6
logically structured answer with linkages and fully-sustained
reasoning.

Marks are awarded for indicative content and for how the answer
is structured and shows lines of reasoning.

The following table shows how the marks should be awarded for The mark for indicative content should be added to the
indicative content. mark for lines of reasoning. For example, an answer
Number of indicative marking Number of marks awarded with five indicative marking points that is partially
points seen in answer for indicative marking points structured with some linkages and lines of reasoning
6 4 scores 4 marks (3 marks for indicative content and 1
5-4 3 mark for partial structure and some linkages and lines of
3-2 2 reasoning).
1 1
0 0 If there are no linkages between points, the same five
indicative marking points would yield an overall score
The following table shows how the marks should be awarded for of 3 marks (3 marks for indicative content and no marks
structure and lines of reasoning. for linkages).
Number of marks awarded
for structure and sustained If there is any incorrect chemistry, deduct mark(s) from
lines of reasoning the reasoning. If no reasoning mark(s) awarded, do not
Answer shows a coherent and deduct mark(s).
logical structure with linkages and 2
fully sustained lines of reasoning Comment: Look for the indicative marking points first,
demonstrated throughout. then consider the mark for the structure of the answer
Answer is partially structured and sustained line of reasoning.
with some linkages and lines of 1
reasoning.
Answer has no linkages between
points and is unstructured. 0
Indicative points:

 IP1: identification of [Ti(H2O)6]3+ complex ion Allow [Ti(H2O)5Cl]2+ / [Ti(H2O)4Cl2]+

 IP2: partially filled d-subshell/d-orbital(s) (in Ti3+) Accept incomplete for partially filled
Accept (Ti3+ is) 1s22s22p63s23p63d1(4s0)
Allow (Ti3+ is) (3)d1

 IP3: splitting in energy of d-subshell/d-orbitals by water/ligands and

water/ligands split the energy of the d-subshell/d-orbitals
Allow ligands cause d-d splitting
Do not award d-orbital (singular)

 IP4: absorption of light/photon/(electromagnetic) radiation (visible) light/photon/(electromagnetic) radiation is

and electronic transition absorbed and
promoting electrons from lower to higher energy
Allow light etc causes d-d transitions

 IP5: origin of observed colour of complex ion colour due to reflected/transmitted light
Allow colour due to wavelengths/frequencies of light
that are not absorbed
Allow complementary colour observed
Do not award any reference to emission of light

 IP6: clearer colour change at end-point with indicator Accept reverse argument
Allow colours are more intense/distinct/sharp/strong
Allow concentration (of [Ti(H2O)6]3+/TiCl3) too low to
accurately determine end-point in absence of indicator
Ignore just easier to determine end-point
Ignore just more accurate/precise
Ignore mention of specific colours, even if incorrect
Do not award reference to acid-base colour change
(Total for Question 20 = 20 marks)
TOTAL FOR SECTION B = 50 MARKS
Section C

Question
Answer Additional guidance Mark
Number
21(a) A completed mechanism showing: Example of completed mechanism: 1

 curly half-arrows to show homolytic fission of OH bond

Accept curly half-arrows originating from

opposite sides of the OH bond

Left-hand curly half-arrow must terminate

between T● and H

Right hand curly half-arrow must terminate on

or near to O atom of HO
Question
Answer Additional guidance Mark
Number
21(b) A completed mechanism showing: Example of completed mechanism: 2

Penalise curly half-arrows once only

 curly arrow from lone pair on Se to correct C of C=C (1) Do not award curly arrow from negative charge on Se

 curly arrow from C=C bond to CC bond Ignore (+)C=C() dipole
Do not award (-)C=C() dipole
and Do not award full charge on either carbon of C=C bond

curly arrow from C=O bond to O (1) Do not award incorrect (-)C=O(+) dipole
Question
Answer Additional guidance Mark
Number
21(c) A completed table showing: Example of completed table: 2

 two or three correct answers (1)

 four correct answers (2)

Question
Answer Additional guidance Mark
Number
21(d)(i) If name and formula given, both must be correct to score M1 2

 K2Cr2O7 and H2SO4 (1) Accept names (eg sodium dichromate((VI)) and sulfuric acid)
Allow Cr2O72 and H+ / acidified dichromate

Ignore concentration of acid

Do not award KMnO4 for K2Cr2O7

Do not award HCl for H2SO4

 heat/reflux (1) M2 dependent on some mention of dichromate (or manganate) oxidising agent
Ignore distillation
Question
Answer Additional guidance Mark
Number
21(d)(ii) Example of correct structure: 1
 correct structure for 2-aminobenzoic acid

Accept hydrochloride salt (NH3Cl)

Allow protonated amine group (NH3+)

Allow any correct combination of skeletal, structural or

displayed formulae

Allow Kekulé benzene

Ignore connectivity
Ignore name, even if incorrect

Question
Answer Additional guidance Mark
Number
21(d)(iii)  NaNO2/sodium nitrite/sodium nitrate(III) Allow HNO2/nitrous acid 1
and Allow H+ and NO2
HCl/hydrochloric acid
Ignore conditions, including concentration of HCl
Ignore H2O

Do not award NaNO3/sodium nitrate

Question
Answer Additional guidance Mark
Number
21(d)(iv) Example of correct structure: 1
 correct structure for N,N-dimethylphenylamine

Allow any correct combination of skeletal, structural or

displayed formulae

Allow Kekulé benzene

Ignore quaternary salt (N(CH3)3+)

Ignore name, even if incorrect

Question
Answer Additional guidance Mark
Number
21(d)(v) An explanation including: 2

 effect of temperature higher than 5C (1) (diazonium/it) decomposes / reacts with water / forms a phenol /
undergoes nucleophilic substitution (above 5C)

Ignore byproducts form / side reactions occur / yield too low (above 5C)

 effect of temperature lower than 5C (1) (rate of reaction) too slow (below 5C)
Allow just slows down (below 5C)

Ignore insufficient energy for reaction to occur (below 5C)

Ignore any reference to activation energy/collision frequency
Ignore freezes (at 0C and below)
Question
Answer Additional guidance Mark
Number
21(e)(i) A completed equation showing: Example of equation: 2

 correct balancing of propanone and

sodium ethanoate (1)

 correct balancing of sodium hydroxide M2 dependent on M1

and water (1)
Question
Answer Additional guidance Mark
Number
21(e)(ii) Correct answer with no working scores (3) 3

Example of calculation:
M1: molar masses
 M(2-nitrobenzaldehyde) M(2-nitrobenzaldehyde) = 7  12.0 + 5  1.0 + 1  14.0 + 3  16.0
and = 151(.0 g mol1)
M(indigotin) (1) M(indigotin) = 16  12.0 + 10  1.0 + 2  14.0 + 2  16.0
= 262(.0 g mol1)

Then, for M2 and M3, either: Allow truncation of mass/moles throughout, eg 0.03816 for 0.038168
Ignore SF except 1 SF in M2 and M3

Method 1 (M2 and M3)

 moles indigotin in 10.0 g moles indigotin in 10.0 g = 10.0 = 0.038168
262
TE on M(indigotin)
and
indigotin:2-nitrobenzaldehyde mol ratio (1) moles 2-nitrobenzaldehyde = 2  0.038168 (= 0.076336)
TE on moles indigotin

 moles 2-nitrobenzaldehyde required moles 2-nitrobenzaldehyde required = 100  0.076336

85
= 0.089807
and
mass 2-nitrobenzaldehyde required (1) mass 2-nitrobenzaldehyde required = 0.089807 × 151
= 13.561
= 14 (g)
TE on moles 2-nitrobenzaldehyde
TE on M(2-nitrobenzaldehyde)
OR

Method 2 (M2 and M3)

 mass indigotin if 100% yield mass indigotin if 100% yield = 100  10.0
85
= 11.765 (g)
and
moles indigotin if 100% yield (1) moles indigotin if 100% yield = 11.765 = 0.044903
262
TE on M(indigotin)

 indigotin:2-nitrobenzaldehyde mol ratio moles 2-nitrobenzaldehyde = 2  0.044903 (= 0.089807)

TE on moles indigotin
and
mass 2-nitrobenzaldehyde (1) mass 2-nitrobenzaldehyde = 0.089807 × 151
= 13.561
= 14 (g)
TE on moles 2-nitrobenzaldehyde
TE on M(2-nitrobenzaldehyde)
Question
Answer Additional guidance Mark
Number
21(f)(i) A drawing showing: Example of drawing: 2

 hydrolysed ester linkage

and
correct carbon frame and amine group (1)

 deprotonated carboxylic acid and phenol groups (1)

Allow ONa
Do not award ONa

Allow E isomer
Allow Kekulé benzene

Allow any correct combination of skeletal,

structural or displayed formulae
Question
Answer Additional guidance Mark
Number
21(f)(ii) A drawing showing: Example of drawing: 1

 correct condensation product

Allow Kekulé benzene

Allow any correct combination of skeletal,

structural or displayed formulae

Allow diacylated product, ie

Total for Section C = 20 marks

Total for Paper = 90 marks
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