GCE

Chemistry A

H432/02: Synthesis and analytical techniques

Advanced GCE

Mark Scheme for November 2020

Oxford Cambridge and RSA Examinations

OCR (Oxford Cambridge and RSA) is a leading UK awarding body, providing a wide range of
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support, which keep pace with the changing needs of today’s society.

This mark scheme is published as an aid to teachers and students, to indicate the requirements
of the examination. It shows the basis on which marks were awarded by examiners. It does not
indicate the details of the discussions which took place at an examiners’ meeting before marking
commenced.

All examiners are instructed that alternative correct answers and unexpected approaches in
candidates’ scripts must be given marks that fairly reflect the relevant knowledge and skills
demonstrated.

Mark schemes should be read in conjunction with the published question papers and the report
on the examination.

© OCR 2020

Oxford Cambridge and RSA Examinations

1. Annotations available in RM Assessor

Annotation Meaning
Correct response

Incorrect response

Omission mark

Benefit of doubt given

Contradiction

Rounding error

Error in number of significant figures

Error carried forward

Level 1

Level 2

Level 3

Benefit of doubt not given

Noted but no credit given

Ignore
2. Abbreviations, annotations and conventions used in the detailed Mark Scheme (to include abbreviations and subject-specific conventions).

Annotation Meaning

DO NOT ALLOW Answers which are not worthy of credit

IGNORE Statements which are irrelevant

ALLOW Answers that can be accepted

() Words which are not essential to gain credit

__ Underlined words must be present in answer to score a mark

ECF Error carried forward

AW Alternative wording

ORA Or reverse argument

H432/02 Mark Scheme November 2020

1. Subject-specific Marking Instructions

INTRODUCTION

Your first task as an Examiner is to become thoroughly familiar with the material on which the examination depends. This material includes:

• the specification, especially the assessment objectives

• the question paper

• the mark scheme.

You should ensure that you have copies of these materials.

You should ensure also that you are familiar with the administrative procedures related to the marking process. These are set out in the OCR
booklet Instructions for Examiners. If you are examining for the first time, please read carefully Appendix 5 Introduction to Script Marking:
Notes for New Examiners.

Please ask for help or guidance whenever you need it. Your first point of contact is your Team Leader.

4
H432/02 Mark Scheme November 2020

SECTION A

AO
Question Answer Marks Guidance
element
1 A 1 1.2
2 B 1 1.1
3 A 1 1.1
4 C 1 2.3
5 D 1 1.2
6 D 1 2.1
7 A 1 1.1
8 C 1 2.2
9 D 1 1.2
10 C 1 2.5 ALLOW 5
11 A 1 2.6
12 A 1 2.2
13 A 1 1.1
14 B 1 2.3
15 C 1 1.2

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H432/02 Mark Scheme November 2020

SECTION B

AO
Question Answer Marks Guidance
element
16 (a) (i) 2-bromo-3,3-dimethylbutane  1 1.2 IGNORE lack of hyphens or addition of commas

ALLOW 3,3-dimethyl-2-bromobutane

DO NOT ALLOW
2-bromo-3-dimethylbutane
methy for methyl
methly for methyl
brom for bromo
(b) (i) Stereoisomers 1 1.2 ALLOW structure/displayed/skeletal formula
Same structural formula
AND DO NOT ALLOW same empirical formula
Different arrangement (of atoms) in space OR same general formula
OR different spatial arrangement (of atoms)
AND IGNORE same molecular formula
Type: Optical  IGNORE references to chiral
molecules/compounds

(ii) One 3D structure with correct groups attached to the 2 2.5 ALLOW small slip in one of the groups OR use of
chiral C  C4H9
3D structures must have four central bonds with at
1.2 least two wedges.

Two 3D structures of (CH3)3CCHBrCH3 that are mirror For bond into paper accept:
images AND correct connectivity in both 

Br Br

C C ALLOW two 3D structures with 2 groups swapped

CH3 H3C e.g.
(CH3 )3 C C(CH3)3
H H
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
Br Br

C C
CH 3 C(CH3 )3
(CH 3) 3C H3 C
H H

(c) 3 ALLOW Br2 → Br• + Br•

Initiation IGNORE dots for initiation step,
Br2 → 2Br•  1.2 i.e. ALLOW Br2 → Br + Br OR Br2 → 2Br

Propagation

DOT REQUIRED at correct position on chain.

+ Br• + HBr
ALLOW 1 mark if both propagation equations are
 2.5×2 correct by atom but dot(s) missing or on incorrect
C in chain

ALLOW 1 mark if both propagation equations are

correct including position of dot(s) but structures
are not shown using skeletal formula

ALLOW ECF from incorrect intermediate

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H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element

(d) further substitution/s 2 1.1×2 ALLOW dibromo/multibromo compounds formed

OR OR an example of a further substitution product
produces different termination products OR an example of a different termination product
OR ALLOW more than one hydrogen (atom) can be
More than one termination step replaced
OR ALLOW radicals react with each other to form
Mixture of products are formed  other products
IGNORE references to separation of products
IGNORE references to atom economy or yield

substitution at different positions along chain  ALLOW a hydrogen (atom) on a different carbon
(atom) can be replaced

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H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
17 (a) (i) 2 2.5×2

 
Organic product with B Organic product with C

(ii) Reactivity of B 3 1.1×3 ALLOW labelled diagram to show

in B electrons are localised delocalised system
OR
in B π-bond is localised 

Reactivity of C
in C electrons are delocalised
OR
In C π-system / ring is delocalised

In B, electron density is higher IGNORE charge density

AND IGNORE electronegativity
B is more susceptible to electrophilic attack
OR IGNORE B is more reactive/reacts more
B attracts/accepts the electrophile/Cl2 more readily (no reference to electrophile)
OR
B polarises the electrophile/Cl2 more  IGNORE references to electron density
ORA spread around the π−ring

ALLOW chlorine

9
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(iii) Generation of electrophile 5 ANNOTATE ANSWER WITH TICKS AND
1.2 CROSSES
AlCl3 + Cl2 → AlCl4– + Cl+  ALLOW FeCl3 + Cl2 → FeCl4– + Cl+
ALLOW use of Fe
Attack of Cl+
NOTE: curly arrows can be straight, snake-
like, etc.
……….. but NOT double-headed or half-
headed arrows

1st curly arrow must

Curly arrow from π-bond to Cl  + 1.2 • start from, OR close to, circle of
--------------------------------------------------------------- benzene ring
Intermediate and organic product

DO NOT ALLOW following intermediate:

2.5
Correct intermediate 

Curly arrow from C–H bond to reform π-ring  π-ring must cover 4 of the 6 sides of the
1.2
benzene ring
AND
------------------------------------------------------------- correct orientation, i.e. gap towards C–Cl
Regeneration of catalyst
H+ + AlCl4– → AlCl3 + HCl  1.2 ALLOW + sign anywhere inside the
‘hexagon’ of the intermediate.

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H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
IGNORE partial charges on the chlorine in
the intermediate

DO NOT ALLOW mark for intermediate if

any CH3 is missing

Curly arrow must start from, OR be traced

back to, any part of C-H bond and go
inside the ‘hexagon’

ALLOW use of AlCl4- in the mechanism

ALLOW ECF for regeneration of an

incorrect metal chloride catalyst e.g. AgCl3
(b) 3C3H6O → C9H12 + 3H2O 3

molecular formulae of C3H6O AND C9H12  2.6

H2O as by-product  2.5

correct balanced equation  2.6

(c) (i) Compound C Compound D 2 3.2

Number of peaks 3 8

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H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(ii) 5 ALLOW any combination of skeletal OR
3.2×5 structural OR displayed formula as long as
unambiguous

IGNORE names for organic intermediates


(question asks for structures
 ALLOW names of reagents and catalyst

Around top arrow, ALLOW 1 of 2 marks if
HNO3 and H2SO4 swapped.
i.e.

IGNORE references to concentration

 ALLOW (CH3CO)2O for left arrow

IGNORE CH3COOH
IGNORE acyl chloride

DO NOT ALLOW AlCl3/FeCl3/Fe4

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H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
18 (a) (i) Reagents 3 ALLOW Na2Cr2O7 OR Cr2O72–
K2Cr2O7 AND acid ALLOW H2SO4 OR HCl OR H+
AND reflux  1.1 ALLOW words. e.g. ‘acidified dichromate’
ALLOW a small slip in formula for dichromate
Equation e.g KCr2O7,
HO(CH2)4OH + 4[O] → HOOC(CH2)2COOH + 2H2O

[O] AND H2O  2.5

Correctly balanced equation  2.6

(ii) O O 2 ALLOW any combination of skeletal OR
hydrogen/H bond
2.1×2 structural OR displayed formula as long as
C (CH2)2 C
δ+ δ– H unambiguous
HO O H O
DO NOT ALLOW δ+ on H atoms of CH2 group
H
OR ALLOW H-bond for hydrogen bond

ALLOW H bond between C=O and H2O, i.e.

Diagram showing correct dipole charges on each end of

one hydrogen bond between a water molecule and a
diacid 

Hydrogen bond between one lone pair on O atom in one

of the molecules and the H atom of another IF diagram is not labelled, ALLOW hydrogen
AND bond/H bond from text
Hydrogen bonding stated or labelled on diagram

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H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(b) (i) 2 ALLOW the ‘O’ or C=O at either end, e.g.
O O

C (CH2)2 C O (CH2)4 O

1.2
Ester link (must be displayed) 
2.5 IGNORE brackets
Rest of structure 
IGNORE n
End bonds’ MUST be shown (solid or dotted)

DO NOT ALLOW more than one repeat unit

(ii) the ester/ ester bond/ ester group /polyester can be 1 3.2 IGNORE references to photodegradable
broken down 
‘Bond breaks’ is not sufficient – no reference to
OR ester bond

It can be hydrolysed 
(iii) 3 ALLOW alternative approach using PCl5 or
PCl3

SOCl2 in equation  1.1

Structure of diacyl dichloride  1.2

Complete balanced equation  2.6

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H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
19 (a) (i) (series of organic compounds with the) same functional 2 1.1 IGNORE reference to physical properties
group OR same/similar chemical properties/reactions  ×2 IGNORE same general formula
DO NOT ALLOW same empirical OR
molecular formula
each successive/subsequent member differs by CH2  Differs by CH2 is not sufficient (no successive)

(ii) C24H48O  1 2.1

(b) F/aldehyde 4 IGNORE use of 2,4-DNP with F

AND
Tollens’ (reagent)
AND ALLOW ammoniacal silver nitrate OR Ag+/NH3
Silver (mirror/precipitate/ppt/solid)  2.3 ALLOW black ppt OR grey ppt

G/alkene/C=C
AND
Bromine/Br2 ALLOW bromine water/ Br2(aq)
AND
goes colourless/decolourised  3.3

G/ketone ALLOW errors in spelling for 2,4-DNP

AND ALLOW 2,4(-)DNP OR 2,4(-)DNPH
2,4-dinitrophenylhydrazine ALLOW Brady’s reagent or Brady’s Test
AND ALLOW solid OR crystals OR ppt as
orange/yellow/red precipitate  3.3 alternatives for precipitate

G/ketone ALLOW ammoniacal silver nitrate OR Ag+/NH3

AND ALLOW black ppt OR grey ppt
Tollens’ (reagent)
AND ALLOW alterative approach using acidified
no silver mirror/no change/no reaction  3.3 potassium dichromate for tests with F and/or G,
with correct observations, alongside use of 2,4-
DNP

15
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(c) (i) Mechanism 3 marks 5 ANNOTATE ANSWER WITH TICKS AND
CROSSES

Curly arrow must come from lone pair on C

of –CN OR CN–
OR from minus sign on C of –CN ion (then lone
pair on CN– does not need to be shown)

Curly arrow from C=O bond must start from,

Curly arrow from –CN to C atom of C=O  1.2 OR be traced back to, any part of C=O bond
and go to O
Dipole shown on C=O bond, Cδ+ and O δ−,
AND curly arrow from C=O bond to O atom  1.2

Curly arrow from lone pair OR – charge on O– of -------------------------------------------------------------

correct intermediate to H+  2.5 ALLOW curly arrow to H atom of H2O, i.e.
-----------------------------------------------------------
Product 1 mark

IGNORE attempt to draw curly arrow showing

 2.5 breaking of H–O in H2O
--------------------------------------------------------
Name of mechanism 1 mark IGNORE lack of dipole on H2O
Nucleophilic addition  1.1

16
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(ii) Heterolytic 2 1.2 ALLOW 2 electrons go to one (bonded)
One (bonded) atom/O receives both/2 electrons  atom/O
DO NOT ALLOW both pairs of electrons go to
Fission O
Breaking of a covalent bond 
IGNORE formation of ions/radicals

For O atom,
ALLOW species
DO NOT ALLOW element or molecule
ALLOW π bond in C=O breaks

IGNORE breaking of C=O bond (no reference

to only one bond breaking)

‘Bond breaking’ is not sufficient

(no reference to covalent)

17
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
20 (a)* Refer to marking instructions on page 4 of mark scheme 6 2.8×2 Indicative scientific points may include:
for guidance on marking this question. 3.3×4 Calculation of mass of cyclopentanol
Using moles
Level 3 (5-6 marks) 4.00
• n(cyclopentene) = = 0.0588…. (mol)
A correct calculation of the mass of cyclopentanol 68
AND 100
• n(cyclopentanol) = 0.0588 × = 0.0919…(mol)
A detailed description of most purification steps 64
• Mass of cyclopentanol = 86 × 0.0919 = 7.90 g
There is a well-developed line of reasoning which is
Using mass
clear and logically structured. The information presented 100
is relevant and substantiated. • Theoretical mass cyclopentene= 4.00 × = 6.25 g
64
6.25
Level 2 (3-4 marks) • Theoretical n(cyclopentanol) = = 0.0919 (mol)
68
Calculates the mass of cyclopentanol with some errors • Mass of cyclopentanol = 86 × 0.0919 = 7.90 g
AND
A detailed description of some purification steps ALLOW for small slip in Mr / rounding errors
OR
A correct calculation of the mass of cyclopentanol Examples of some calculation errors
AND Incorrect inverse ratio:
A detailed description of a few purification steps 64
• 0.0588 × = 0.0376…. (mol)
100
There is a line of reasoning presented with some • Mass = 86 × 0.0376 = 3.24 g
structure. The information presented is relevant and
Ignoring % yield gives:
supported by some evidence. 4.00
• = 0.0588…. (mol)
68
Level 1 (1-2 marks) • Mass = 86 × 0.0588 = 5.06 g
Calculates the mass of cyclopentanol with some errors
OR Purification
A detailed description of some purification steps • Add a neutralising agent by formula or name e.g.
Na2CO3
There is an attempt at a logical structure with a line of • In separating funnel, organic layer is on top
reasoning. The information is in the most part relevant. • Drying with an anhydrous salt by formula or
name, e.g. MgSO4, Na2SO4, CaCl2
0 marks No response or no response worthy of • Redistil at approx. 44ºC
credit. Examples of detail in bold (NOT INCLUSIVE)

18
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(b) C=C/alkene peak in region 1620-1680 cm–1  2 3.2×2 LOOK ON THE SPECTRUM for labelled peaks
which can be given credit
O–H/alcohol peak in region 3200-3600 cm–1 
IGNORE references to C-O at 1000cm-1

19
 H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
21 (a) 5 2.5×5 ALLOW any combination of skeletal OR structural OR
displayed formula as long as unambiguous

ALLOW HBr


ALLOW for the bottom left structure




20
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(b) (i) Ester 3 1.2×3
Amide IGNORE amino acid
Amine
Carboxylic acid ALLOW carboxyl
4 groups correct 
3 groups correct  IGNORE attempt to classify amide, e.g. secondary
2 groups correct  IGNORE formulae (question asks for names)

IF > 4 functional groups are shown,

• Count 4 groups max but incorrect groups first

IGNORE aryl OR alkyl group

e.g. benzene, phenyl, aryl, arene, methyl
(ii) Methanol 1 mark 4 2.5×4 ALLOW any combination of skeletal OR structural OR
displayed formula as long as unambiguous


Amino Acids 3 marks

ALLOW + charge on H of NH3 group, i.e.NH3+


If BOTH amino acids are shown with NH3 groups
(without the + charge) OR as NH2+ groups,
award 2 of the 3 marks for the amino acids

If BOTH amino acids are shown as correctly balanced


salts, e.g NH3Cl, all marks can be awarded.

Both amino acids shown with NH3+ 

21
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
(iii) FIRST CHECK ANSWER ON THE ANSWER LINE 3 2.2×3 If there is an alternative answer, apply ECF and
If answer = 22.4 OR 22 OR 23 award 3 marks look for alternative methods

n(aspartame) in 1 can = 0.167 / 294 = 5.68 x 10-4 (mol)  Alternative methods

n(aspartame) in 1 can = 0.167 / 294
n(aspartame) limit per day = 1.7x10-4 x 75 = 0.01275 = 5.68 x 10-4 (mol) 
(mol) 
n(aspartame) per kg = 5.68 x 10-4 / 75
number of cans = 0.01275 / 5.68 x 10 = 22.4 
-4
= 7.57 x 10-6 (mol) 

number of cans = 1.7 x 10-4 / 7.57 x 10-6

= 22.4

OR

n(aspartame) limit per day = 1.7x10-4 x 75

=0.01275 (mol) 

mass(aspartame) limit per day =0.01275 x 294

= 3.7485 (g) 

number of cans = 3.7485 / 0.167

= 22.4 

22
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element
22 (a) CDCl3 used as a solvent  2 1.1×2 Example and use required for each mark

D2O used to identify OH OR NH protons  ALLOW for 1 mark, D2O as a solvent

(b)* Please refer to the marking instructions on page 4 of this mark 6 3.1× 4 Indicative scientific points:
scheme for guidance on how to mark this question. 3.2× 2 Empirical and Molecular Formulae
C : H : N : O
Level 3 (5–6 marks) 56.69 7.09 11.02 25.20
= : : :
Structure I has a viable chemical structure of C6H9NO2 which 12.0 1.0 14.0 16.0
has the key features consistent with spectral data OR 4.72 : 7.09 : 0.787 : 1.575
AND = 6 : 9 : 1 : 2
Most of the data analysed
• Empirical formula = C6H9NO2
There is a well-developed line of reasoning which is clear and • m/z = 127.0 and empirical formula
logically structured. The information presented is relevant and
substantiated. mass (127) used to determine
molecular formula as C6H9NO2
Level 2 (3–4 marks)
Compound I has a viable chemical structure of C6H9NO2 with Structures of compound I
most of the key features consistent with spectral data
AND
Some of the spectral data analysed.

There is a line of reasoning presented with some structure. The OR

information presented is relevant and supported by some
evidence. OR
Level 1 (1–2 marks)
Correct determination of empirical formula and/or molecular
formula. OR
OR
Analyses some of the IR and NMR data. ALLOW any combination of skeletal OR
OR structural OR displayed formula as long as
Analyses most of the NMR data. unambiguous

23
H432/02 Mark Scheme November 2020

AO
Question Answer Marks Guidance
element

There is an attempt at a logical structure with a line of reasoning. Key features

The information is in the most part relevant. • C ≡N
• C=O in aldehyde, ketone, ester,
0 marks No response or no response worthy of credit. amide, acid anhydride
• CH3 group that would give a doublet
• CH3 group that would give a triplet
• CH2 group that would give a quartet
1
H NMR and IR analysis
1
H NMR spectrum
• δ = 4.2 ppm, quartet, 2H CH3–
CH2–O
• δ = 2.9 ppm, quartet, 1H CO–CH–
CH3
• δ = 1.7 ppm, doublet, 3H CO–CH–
CH3
• δ = 1.3 ppm, triplet, 3H CH3–CH2

IR spectrum
• peak at 1750 (cm–1) is C=O
• peak at 2280 (cm–1) is C ≡N
ALLOW ranges from Data Sheet
IGNORE references to C–O peaks

24
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