Mark Scheme Synthesis and Analytical Techniques

GCE
Chemistry A
H432/02: Synthesis and analytical techniques
A Level
Mark Scheme for June 2022
Oxford Cambridge and RSA Examinations

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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 2022
Oxford Cambridge and RSA Examinations

H432/02 Mark Scheme June 2022
MARKING INSTRUCTIONS
PREPARATION FOR MARKING
RM ASSESSOR
1. Make sure that you have accessed and completed the relevant training packages for on-screen marking: RM Assessor Online Training; OCR
Essential Guide to Marking.
2. Make sure that you have read and understood the mark scheme and the question paper for this unit.
3. Log-in to RM Assessor and mark the required number of practice responses (“scripts”) and the required number of standardisation
responses.
MARKING
1. Mark strictly to the mark scheme.
2. Marks awarded must relate directly to the marking criteria.
3. The schedule of dates is very important. It is essential that you meet the RM Assessor 50% and 100% (traditional 50% Batch 1 and 100%
Batch 2) deadlines. If you experience problems, you must contact your Team Leader (Supervisor) without delay.
4. If you are in any doubt about applying the mark scheme, consult your Team Leader by telephone, email or via the RM Assessor messaging
system.
5. Work crossed out:
Crossed Out Responses

Where a candidate has crossed out a response and provided a clear alternative then the crossed out response is not marked. Where no
alternative response has been provided, examiners may give candidates the benefit of the doubt and mark the crossed out response where
legible.
2
Rubric Error Responses – Optional Questions

Where candidates have a choice of question across a whole paper or a whole section and have provided more answers than required, then all
responses are marked and the highest mark allowable within the rubric is given. Enter a mark for each question answered into RM assessor, which
will select the highest mark from those awarded. (The underlying assumption is that the candidate has penalised themselves by attempting more
questions than necessary in the time allowed.)
Multiple Choice Question Responses

When a multiple choice question has only a single, correct response and a candidate provides two responses (even if one of these responses is
correct), then no mark should be awarded (as it is not possible to determine which was the first response selected by the candidate).
When a question requires candidates to select more than one option/multiple options, then local marking arrangements need to ensure consistency
of approach.
Contradictory Responses
When a candidate provides contradictory responses, then no mark should be awarded, even if one of the answers is correct.
Short Answer Questions (requiring only a list by way of a response, usually worth only one mark per response)
Where candidates are required to provide a set number of short answer responses then only the set number of responses should be marked. The
response space should be marked from left to right on each line and then line by line until the required number of responses have been considered.
The remaining responses should not then be marked. Examiners will have to apply judgement as to whether a ‘second response’ on a line is a
development of the ‘first response’, rather than a separate, discrete response. (The underlying assumption is that the candidate is attempting to
hedge their bets and therefore getting undue benefit rather than engaging with the question and giving the most relevant/correct responses.)
Short Answer Questions (requiring a more developed response, worth two or more marks)
If the candidates are required to provide a description of, say, three items or factors and four items or factors are provided, then mark on a similar
basis – that is downwards (as it is unlikely in this situation that a candidate will provide more than one response in each section of the response
space.)
Longer Answer Questions (requiring a developed response)

Where candidates have provided two (or more) responses to a medium or high tariff question which only required a single (developed) response and
not crossed out the first response, then only the first response should be marked. Examiners will need to apply professional judgement as to whether
the second (or a subsequent) response is a ‘new start’ or simply a poorly expressed continuation of the first response.
3
6. Always check the pages (and additional objects if present) at the end of the response in case any answers have been continued there. If the
candidate has continued an answer there then add a tick to confirm that the work has been seen.
7. Award No Response (NR) if:
• there is nothing written in the answer space.
Award Zero ‘0’ if:

• anything is written in the answer space and is not worthy of credit (this includes text and symbols).
Team Leaders must confirm the correct use of the NR button with their markers before live marking commences and should check this
when reviewing scripts.
8. The RM Assessor comments box is used by your Team Leader to explain the marking of the practice responses. Please refer to these
comments when checking your practice responses. Do not use the comments box for any other reason.
If you have any questions or comments for your Team Leader, use the phone, the RM Assessor messaging system, or email.
9. Assistant Examiners will send a brief report on the performance of candidates to their Team Leader (Supervisor) via email by the end of the
marking period. The report should contain notes on particular strengths displayed as well as common errors or weaknesses. Constructive
criticism of the question paper/mark scheme is also appreciated.
4
10. For answers marked by levels of response:

Read through the whole answer from start to finish, using the Level descriptors to help you decide whether it is a strong or weak answer. The
indicative scientific content in the Guidance column indicates the expected parameters for candidates’ answers, but be prepared to recognise
and credit unexpected approaches where they show relevance. Using a ‘best-fit’ approach based on the skills and science content evidenced
within the answer, first decide which set of level descriptors, Level 1, Level 2 or Level 3, best describes the overall quality of the answer.
Once the level is located, award the higher or lower mark:
The higher mark should be awarded where the level descriptor has been evidenced and all aspects of the communication statement (in
italics) have been met.
The lower mark should be awarded where the level descriptor has been evidenced but aspects of the communication statement (in italics)
are missing.
In summary:
The skills and science content determines the level.
The communication statement determines the mark within a level.
Level of response questions on this paper are 19(e) and 21
The only annotation on a level of response question should be the indication of the level.
A level annotation should be used where all marks for a level have been achieved.
e.g. if a candidate has 6 marks, they would have this annotation on their script:
If a candidate has achieved 5 marks then they have reached Level 3 but will not have met the communication statement.
They should have the following annotations on their scripts:
The same principle should be applied to Level 2 and Level 1.

No marks (0) should have a cross:
Place the annotations alongside the mark for the question.
On additional pages, annotate using
5
11. 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
Blank page
6
12. 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
7
13. 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.
8
SECTION A
AO
Question Answer Marks Guidance
element
1 B 1 AO1.1
2 B 1 AO1.1
3 D 1 AO1.2 ALLOW 15 (correct number of sigma bonds)
4 A 1 AO1.1
5 D 1 AO1.2 ALLOW 8 (correct number of chiral centres)
6 B 1 AO1.2
7 D 1 AO1.2
8 C 1 AO2.2 ALLOW 500 (This is the correct mass)
9 C 1 AO2.6 ALLOW 4.8 (This is the correct volume)
10 B 1 AO1.2
11 B 1 AO2.5
12 A 1 AO2.1
13 D 1 AO1.1
14 A 1 AO1.1
15 B 1 AO2.1
Total 15
9
SECTION B
AO
element
16 (a) (i) 3-methylhex-2-ene  1 AO1.2 IGNORE lack of hyphens, or addition of commas
DO NOT ALLOW 3-methyhex-2-ene

OR 3-methhex-2-ene
OR 3-methlyhex-2-ene
OR 3-methylhexan-2-ene
IGNORE references to E/Z or cis/trans

16 (a) (ii) ANNOTATE ANSWER WITH TICKS AND CROSSES 3 AO1.2 ALLOW any combination of skeletal OR structural
×1 OR displayed formula as long as unambiguous
AO2.5 IGNORE connectivity of CH3CH2CH2 and CH3

×2 groups in carbocation and product
ALLOW C3H7 for CH3CH2CH2
DO NOT ALLOW half headed or double headed

arrows but allow ECF if seen more than once
DO NOT ALLOW use of HBr but ECF for

subsequent use
Curly arrow from C=C bond to Brδ+ of Br–Br For curly arrows, ALLOW straight or snake-like
arrows and small gaps (see examples):
AND ------------------------------------------------------------
Correct dipole on Br–Br DO NOT ALLOW partial charge on C=C

AND
curly arrow for breaking of Br–Br bond  1st curly arrow must
• go to a Br atom of Br–Br
AND
start from, OR be traced back to any point across
width of C=C
AO
element
2nd curly arrow must

• start from, OR be traced back to, any part
of δ+Br–Brδ– bond
• AND go to Br δ–
Correct carbocation to match mechanism 3rd curly arrow must

AND curly arrow from Br– to C+ of carbocation • go to the C+ of carbocation
AND
• start from, OR be traced back to any point
across width of lone pair on :Br–
• OR start from – charge on Br– ion
OR 
(Lone pair NOT needed if curly arrow shown
i.e. ALLOW carbonium + on either C atom
from – charge on Br–)
ALLOW bromonium ion (Contact TL)

--------------------------------------------------------------------------
11
AO
element
Correct product to match mechanism 
16 (b) (i) Same molecular formula 1 AO1.1 Same formula is not sufficient
AND (no reference to molecular)
Different structural formulae  Different arrangement of atoms is not sufficient
(no reference to structure/structural)
OR For ‘structural formulae’,

ALLOW structure/displayed/skeletal formulae/
Both have the molecular formula C6H12 functional groups
AND
Different structural formulae  DO NOT ALLOW any reference to spatial/space
16 (b) (ii) Same structural formula 1 AO1.1 ALLOW structure/displayed/skeletal formula

AND
Different arrangement (of atoms) in space DO NOT ALLOW same empirical formula
OR different spatial arrangement (of atoms)  OR same general formula
IGNORE same molecular formula
Reference to E/Z isomerism or optical isomerism is

not sufficient
12
AO
element
16 (b) (iii) Correct identification of cis AND trans isomers of 2 ALLOW any combination of skeletal OR structural
4-methylpent-2-ene  AO1.2 OR displayed formula as long as unambiguous
H H H 3C H
AO2.5
C C C C C3H7 is not sufficient (could be unbranched)
H 3C CH(CH3 )2 H CH(CH3 )2 ALLOW one mark if cis AND trans isomers of

4-methylpent-2-ene are in the wrong boxes
cis isomer trans isomer
OR
ALLOW the isomers of 3-methylpent-2-ene in either
Identification of 3-methylpent-2-ene as cis AND trans
box
isomers 

Ambiguity with cis/trans identification system
ALLOW one mark for correct identification of cis

AND trans isomers of unbranched C6H12
e.g.
13
AO
element
16 (b) (iv) Correct groups attached to chiral carbon of compound C 2 AO2.5 ALLOW any combination of skeletal OR structural
seen once e.g. ×2 OR displayed formula as long as unambiguous
For C2H5–, ALLOW CH3CH2–

For –CH=CH2, ALLOW –C2H3 OR –CHCH2
For bond into paper accept:
OR 
Two 3D structures of compound C that are mirror images ALLOW two 3D structures with 2 groups swapped
with correct connectivity in both e.g.
OR 
DO NOT ALLOW a bond angle of 180°

e.g.
14
AO
element
16 (b) (v) 4
ALLOW 1 mark for structures if shown in wrong
boxes.
AO2.5
×2


D E
Two of the following for D  CHECK table 16.1 for annotations that may be
• All H are equivalent/in the same chemical AO2.2 worthy of credit
environment/ the same type ×2
• All C are equivalent/ in the same chemical
environment/ the same type
• No C=C present
Two of the following for E 

• All H are equivalent/ in the same chemical
environment/ the same type
• 2 C environments
• C=C present
15
AO
element
16 (c) (i) 2 AO3.1 ALLOW any combination of skeletal OR structural
×1 OR displayed formula as long as unambiguous
BOTH structures required for 
AO3.2
×1
16 (c) (ii) 1 AO3.2 ALLOW any combination of skeletal OR structural

OR displayed formula as long as unambiguous
Total 17
16
AO
element
17 FIRST CHECK ANSWER LINES 6 AO1.2 ALLOW ECF throughout
If M=168(.0) Award 4 marks for calculation providing ×1
unit conversions are correct ALLOW calculator value of 167.968115 (using
AO2.4 8.314) for M
--------------------------------------------------------------------- ×3 ALLOW calculator value of 167.8873033 (using
Use of ideal gas equation 8.31) for M
pV AO2.5
pV= nRT OR n = RT 
×2
pV
SI Unit conversions AND substitution into n =
RT :
• R = 8.314 OR 8.31
• V = 186 × 10–6
• T in K: 303 K
1.07 × 105 × 186 × 10–6
e.g.  Calculator value of n:
8.314 × 303
from 8.314 = 7.900308915 × 10–3
Calculation of n from 8.31 = 7.904111711 × 10–3
n = 7.90 × 10–3 (mol) 
Calculation of M
1.327
M= = 168(.0) 
7.90 × 10–3
Molecular formula ALLOW ECF that matches M but the formula

C3H2F6O  MUST contain F6O
------------------------------------------------------------
Use of 24 dm3:
186.0
e.g. n =
24000 = 7.75 × 10
–3
No mark
(calculation much simpler)
1.327
M = = 171(.2)  ECF
7.75 × 10–3
C3H5F6O  ECF
17
AO
element
Structure ALLOW ECF for a feasibile chemical structure

that matches M AND contains F6O AND has a
chiral carbon
DO NOT ALLOW
OR
F F
F
F
F O
no chiral carbon
F 
Total 6
18
AO
element
18 (a) (i) (Add) 2,4-dinitrophenylhydrazine AND orange/yellow/red 3 AO1.2 ALLOW errors in spelling
precipitate  ×3 ALLOW 2,4(-)DNP OR 2,4(-)DNPH
ALLOW Brady’s reagent or Brady’s Test
ALLOW solid OR crystals OR ppt as alternatives
for precipitate
Take melting point (of crystals)  Mark second and third points independently of
response for first marking point
Compare to known values/database 
DO NOT ALLOW 2nd and 3rd marks for taking and
comparing boiling points OR chromatograms
18 (a) (ii) Tollens’ (reagent) 1 AO1.2 ALLOW ammoniacal silver nitrate OR Ag+/NH3
AND
Silver (mirror/precipitate/ppt/solid)  ALLOW black ppt OR grey ppt
ALLOW Cr2O72–/H+
AND
Turns green 
IGNORE reference to conditions,

e.g. Heat or reflux
-------------------------------------------------------------
IF other reagents are seen e.g. Fehling’s or
Benedict’s, contact your Team Leader
19
AO
element
18 (b) Initial ratios 4 CHECK spectra for annotations that may be
62.07 10.34 27.59 worthy of credit
C, 12.0 : H, 1.0 : O, 16.0
OR
C, 5.1725 : H, 10.34 : O, 1.724
OR
C, 3 : H, 6 : O, 1  AO1.2 Mark can be awarded from a correct molecular
formula
AO2.5
(Molecular formula =) C3H6O
AND
Evidence of 58 in working or from labelled peak in one of
the spectra AO3.2
For F
evidence for fragment ion m/z=29 linked to CH3CH2(+) AO3.2 IGNORE m/z=15 (as this is not unique)
OR CHO(+)  IGNORE m/z=43
IGNORE incorrect fragments

IGNORE charges on fragment ions
ALLOW any combination of skeletal OR structural

F= OR displayed formula as long as unambiguous
AND
G= 
20
AO
element
18 (c) H NMR
1
4 AO3.1 ALLOW any combination of skeletal OR
×3 structural OR displayed formula as long as
δ = 1.1 ppm/doublet linked to 2 x CH3 unambiguous
CHECK spectra for annotations that may be

worthy of credit
ALLOW δ values ± 0.2 ppm, as a range or a value

within the range
δ = 2.2 ppm/singlet linked to CH3–C=O AO3.2 IGNORE HC–C=O linked to δ = 2.2 ppm
OR ×1
δ = 2.9 ppm/multiplet linked to CH(CH3)2 OR HC–C=O  IGNORE additional chemical environments (taken
from the data sheet) that align with the given
chemical shifts
Structure
Any structure with molecular formula C6H10O2 and has 2

carbonyl groups 
Total 12
21
AO
element
19 (a) C2H5COOH + KOH → C2H5COOK + H2O  4 AO2.6 ALLOW any combination of skeletal OR
unambiguous
IGNORE state symbols and use of equilibrium

sign
ALLOW KC2H5COO
DO NOT ALLOW a missing charge (e.g.

C2H5COO–K) the 1st time seen but IGNORE for
next equations.
2HCOOH + Mg → (HCOO)2Mg + H2  For salts,

ALLOW C2H5COO–K+ OR C2H5COO– + K+
DO NOT ALLOW –COO–K (covalent bond)

the 1st time seen but IGNORE for next
equations.
H2O AND CO2  FOR CO2 + H2O ALLOW H2CO3
Correct formula of salt: 
22
AO
element
19 (b) 4 AO2.5 ALLOW any combination of skeletal OR
unambiguous
ALLOW any vertical bond to the OH group

e.g. ALLOW

 OR
OH HO
IGNORE connectivity of CH3CH2 group
IGNORE inorganic by-products
ALLOW HCl/H2O, H2SO4/H2O

 IGNORE dilute
23
AO
element
19 (c) (i) Pent-3-enoic acid 2 ALLOW any combination of skeletal OR
structural OR displayed formula as long as
unambiguous
 AO1.2 ALLOW either the E or Z isomer
2 repeat units of polymer

ALLOW ECF from pent-2-enoic acid
CH2 COOH CH2 COOH OR pent-4-enoic acid ONLY
H H
For repeat unit,
• ‘side bonds’ required on either side of
C C C C repeat unit from C atoms
• 2 repeat units required
CH3 H CH3 H  AO2.5
IGNORE connectivity of CH2COOH in polymer
IGNORE brackets
IGNORE n
------------------------------------------------------------
ALLOW any consistent repeat unit:
CH2COOH and CH3 groups can alternate or be
on opposite sides of chain
e.g.
CH2 COOH CH2 COOH
H H
C C C C
H CH 3 CH 3 H
24
AO
element
19 (c) (ii) CH3 2 end –O– may be at either side e.g.
CH3
O H H O
O H H O
C C C C O O O C C C C O
H H
H H
AO1.2
ester link 
AO2.5
ALLOW CH3 to be on position 2 or 3 of the
ONE repeat units of correct polymer  aromatic ring
‘End bonds’ MUST be shown (do not have to

be dotted)
IGNORE brackets
IGNORE n
19 (c) (iii) 1 AO3.2 ALLOW any combination of skeletal OR
structural OR displayed formula as long as
unambiguous
19 (d) (i) 1 AO2.5 end –N– may be at either side e.g.

H O H O
N C C C C N
H CH3 CH3 H

‘End bonds’ MUST be shown (do not have to
ONE repeat unit ONLY be dotted)
IGNORE brackets
IGNORE n
25
AO
element
19 (d) (ii) IF answer on answer line = 28418, AWARD 2 marks 2 AO2.2
IF answer on answer line = 28400, AWARD 1 mark ×2
------------------------------------------------------------------------
Mr of 400 molecules = 400 × 89 = 35600  ALLOW ECF from incorrect repeat unit in 19di
Mr of polymer = 35600 – (399 × 18) = 28418  ALLOW ECF from incorrect Mr of 400 repeat
units
Alternative method based on repeat unit:

Mr of 400 repeat units = 400 × 71 = 28400 
Mr of polymer = 28400 + 1 + 17 = 28418 
19 (e)* Refer to marking instructions on page 5 of mark scheme for 6 AO3.3 Indicative scientific points may include:
guidance on marking this question. ×6
Calculation of mass of CH3CHClCOOCH3
Level 3 (5-6 marks) Using moles
Correct calculation of mass of CH3CHClCOOH. 9.36
AND • n(I) =
117.0
Planned synthesis includes substitution of –Cl and formation of = 0.08(00) (mol)
compound I (or its corresponding ammonium salt) with the 100
correct reagents and some conditions identified and equations • n(CH3CHClCOOC2H5) = 0.0800 ×
64
are mostly correct. = 0.125 (mol)
• Mass of CH3CHClCOOH = 108.5 × 0.125
There is a well-developed line of reasoning which is clear and = 13.5625 g
logically structured. The information presented is relevant and
substantiated.
26
AO
element
Level 2 (3-4 marks) Using mass

Calculation of mass of CH3CHClCOOH is correct 100
AND • Theoretical mass of I = 9.36 ×
64
Planned synthesis includes one step of the synthesis with the = 14.625 (g)
correct reagent and some conditions identified and equation is 14.625
mostly correct • Theoretical n(CH3CHClCOOH) =
117.0
OR = 0.125 (mol)
Calculation of mass of CH3CHClCOOH is partly correct • Mass of CH3CHClCOOH = 108.5 × 0.125
AND = 13.5625 g
Planned synthesis includes substitution of –Cl and formation of
compound I (or its corresponding ammonium salt) with the
correct reagents ALLOW slip/rounding errors such as errors in
OR Mr, e.g. use of 107.5 instead of 108.5 for
Attempts to calculate mass of CH3CHClCOOC2H5 but makes little CH3CHClCOOH → 13.4375
progress
AND
Planned synthesis includes substitution of –Cl and formation of ---------------------------------------------------------------
compound I (or its corresponding ammonium salt) with the Examples of partly correct calculations
correct reagents and some conditions identified and equations 64
Mass = 5.5552 g from 0.0800 ×
are mostly correct 100 × 108.5
(% yield inverted)
There is a line of reasoning presented with some structure. The Mass = 8.68 g from 0.0800 × 108.5
information presented is relevant and supported by some (% yield omitted)
evidence.
Synthesis: Either order for 2 stages

Substitution of –Cl → amine:
• Reagents: (excess) NH3
• Condition: ethanol
• Equation: CH3CHClCOOH + 2NH3 →
CH3CHNH2COOH + NH4Cl
OR
CH3CHClCOOH + NH3 →
CH3CHNH2COOH + HCl
27
AO
element
Level 1 (1-2 marks) Esterification of amine → compound I
Calculation of mass of CH3CHClCOOH is partly correct • Reagents: CH3CH2OH
OR • Conditions: acid (catalyst), e.g. H2SO4
Planned synthesis includes both steps with some of the reagents (reflux/heat)
and conditions identified • Equation:
OR CH3CHNH2COOH + CH3CH2OH →
Attempts equations for both steps but these may contain errors CH3CHNH2COOCH2CH3 + H2O
OR OR --------------------------------------------------------
Describes one step of the synthesis with reagents, conditions and Esterification of carboxylic acid → ester
equation mostly correct
• Reagents: CH3CH2OH
• Conditions: acid (catalyst), e.g. H2SO4
There is an attempt at a logical structure with a line of reasoning.
(reflux/heat)
The information is in the most part relevant.
• Equation:
0 marks CH3CHClCOOH + CH3CH2OH →
No response or no response worthy of credit. CH3CHClCOOCH2CH3 + H2O
Substitution of –Cl → amine:
• Reagents: (excess) NH3
• Condition: ethanol
• Equation: e.g
CH3CHClCOOCH2CH3 + 2NH3 →
CH3CHNH2COOCH2CH3 + NH4Cl
OR
CH3CHClCOOCH2CH3 + NH3 →
CH3CHNH2COOCH2CH3 + HCl
OR
CH3CHClCOOCH2CH3 + NH3 →
CH3CHNH3ClCOOCH2CH3
(ammonium salt)
Total 22
28
AO
element
20 (a) (i) Indicator AND observation of acidity 1 AO1.2 ALLOW
AND ×1 (Add) bromine AND white precipitate 
No reaction with carbonate 
ALLOW
(Add) FeCl3 AND violet/purple colour 
20 (a) (ii) Compound J has 3 AO3.2 IGNORE any numbers shown on structures
6 peaks/environments/types of carbon  ×3
IGNORE chemical shifts
Compound K has
5 peaks/environments/types of carbon 
Compound L has
8 peaks/environments/types of carbon 
20 (a) (iii) ANNOTATE ANSWER WITH TICKS AND CROSSES 4 AO1.2
×2
Action of catalyst 1 mark AO2.5 ALLOW use of FeCl3 or other halogen carriers
Formation of electrophile: Cl2 + AlCl3 → Cl + AlCl4–
+
×2 (AlBr3)
AND
Regeneration of catalyst: H+ + AlCl4– → AlCl3 + HCl 
---------------------------------------------------------
--------------------------------------------------------------------------- For curly arrows, ALLOW straight or snake-
Electrophilic attack 1 mark like arrows and small gaps (see examples):
---------------------------------------------------------
Curly arrow from π-bond to Cl+  1st curly arrow must
• start from, OR close to circle of benzene
ring
AND
• go to Cl+
29
AO
element
Correct intermediate only 1 mark DO NOT ALLOW the following intermediate:

π-ring must cover more than half of benzene ring
AND
correct orientation, i.e. gap towards C with Cl
ALLOW + sign anywhere inside the ‘hexagon’ of

intermediate
DO NOT ALLOW intermediates substituted at

positions 3 or 5
IGNORE intermediates substituted at position 2
OR di-substituted at positions 2,4
------------------------------------------------------------------------- ---------------------------------------------------------------
Reforming benzene ring 1 mark Curly arrow must start from, OR be traced back
to, any part of C–H bond and go inside the
Curly arrow from C–H bond to reform π-ring  ‘hexagon’
30
AO
element
20 (b) (In phenols) a (lone) pair of electrons on O is (partially) 3 AO1.1 ALLOW the electron pair in the p-orbitals of the O
delocalised/donated into the ring / π-system  ×3 atom becomes part of the ring / π-system
ALLOW diagram to show movement of lone pair
into ring
ALLOW lone pair of electrons on O is (partially)
drawn/attracted/pulled/ into ring / π-system
ALLOW lone pair on O
DO NOT ALLOW (two) lone pairs are
delocalised/donated into the ring / π-system
Electron density increases/is higher (than benzene)  IGNORE activating

ORA
IGNORE charge density
IGNORE electronegativity
(phenols) are more susceptible to electrophilic attack
OR IGNORE phenols react more readily with
(phenols) attract/accept electrophile/Cl2 more electrophiles/Cl2 (given in question)
OR
(phenols) polarise electrophile/Cl2 more  ALLOW Cl+ for electrophile
ORA IGNORE Cl for electrophile
20 (c) 2 ALLOW any combination of skeletal OR structural

OR displayed formula as long as unambiguous
AO2.5
ALLOW C6H5 for phenyl group
AO2.6
organic product 
Correct balanced equation 
31
20 (d) (i) 2 AO1.2

×2 IGNORE references to concentration

IGNORE ‘dilute’ for HCl

IGNORE H2
IGNORE NaOH if seen as a reagent to convert
nitro group into amine

e.g ‘Sn/(concentrated) HCl then NaOH’ scores the
mark
20 (d) (ii) 1 AO2.6
20 (e) Stage 1 4 ALLOW any combination of skeletal OR structural

Reagents: H2SO4  AO3.1 OR displayed formula as long as unambiguous
ALLOW H+ OR HCl OR H3PO4

DO NOT ALLOW other named acids
IGNORE concentration/pressure
 AO2.6 IGNORE water/steam
Stage 2
Reagents: Steam/H2O(g) AND acid/H+ (catalyst)  AO3.1
For steam,
ALLOW H2O with temperature ≥100ºC
ALLOW use of H3PO4/H2SO4 as catalyst
AO2.6 DO NOT ALLOW HCl
 IGNORE pressure
32
20 (f) 2 ALLOW any combination of skeletal OR structural

Structure of ester product  OR displayed formula as long as unambiguous
AO3.1
Correct balanced equation  AO3.2 ALLOW
Total 22
33
AO
element
21 Refer to marking instructions on page 5 of mark scheme for 6 AO1.2 Indicative scientific points may include:
guidance on marking this question. ×4
Reactions of aliphatic compounds and mechanisms
Level 3 (5–6 marks)
Describes, in detail, reactions of two aliphatic compounds that AO2.5
• Haloalkane, RX and CN– → RCN + X–
form a C–C bond ×2 Reagents: NaCN and ethanol
AND mechanisms for the two aliphatic reactions. Reaction: Nucleophilic substitution
Mechanism:
There is a well-developed line of reasoning which is clear and
logically structured. The information presented is relevant and
substantiated.

Describes a reaction of one aliphatic compound that forms a C–C
bond with few omissions/errors.
AND mechanism for one aliphatic reaction.
OR
Describes reactions of two compounds that forms a C–C bond • Aldehyde or ketone and HCN
AND attempts a mechanism for one of the reactions e.g. RCHO + HCN → RCH(OH)CN
Reagents: NaCN and H+
There is a line of reasoning presented with some structure. The Reaction: Nucleophilic addition
information presented is relevant and supported by some Mechanism:
evidence.

Selects suitable reagents for reactions of two compounds that
form a C–C bond.
OR
Attempts to describe a reaction and mechanism of one compound
that forms a C–C bond, with omissions/errors.
There is an attempt at a logical structure with a line of reasoning.

The information is in the most part relevant. OR H2O instead of H+ for 2nd stage
0 marks No response or no response worthy of credit. If alternative reactions are shown contact your TL
e.g. radical substitution, polymerisation
Total 6
34
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GCE

H432/02: Synthesis and analytical techniques

Mark Scheme for June 2022

Oxford Cambridge and RSA Examinations

Oxford Cambridge and RSA Examinations

PREPARATION FOR MARKING

1. Mark strictly to the mark scheme.

2. Marks awarded must relate directly to the marking criteria.

5. Work crossed out:

Crossed Out Responses

Rubric Error Responses – Optional Questions

Multiple Choice Question Responses

Longer Answer Questions (requiring a developed response)

7. Award No Response (NR) if:

• there is nothing written in the answer space.

Award Zero ‘0’ if:

10. For answers marked by levels of response:

The same principle should be applied to Level 2 and Level 1.

Place the annotations alongside the mark for the question.

On additional pages, annotate using

11. Annotations available in RM Assessor

Benefit of doubt given

Error in number of significant figures

Error carried forward

Benefit of doubt not given

Noted but no credit given

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

ORA Or reverse argument

13. Subject-specific Marking Instructions

• the specification, especially the assessment objectives

• the question paper

• the mark scheme.

You should ensure that you have copies of these materials.

DO NOT ALLOW 3-methyhex-2-ene

IGNORE references to E/Z or cis/trans

AO2.5 IGNORE connectivity of CH3CH2CH2 and CH3

DO NOT ALLOW half headed or double headed

DO NOT ALLOW use of HBr but ECF for

Correct dipole on Br–Br DO NOT ALLOW partial charge on C=C

2nd curly arrow must

Correct carbocation to match mechanism 3rd curly arrow must

ALLOW bromonium ion (Contact TL)

Correct product to match mechanism 

OR For ‘structural formulae’,

16 (b) (ii) Same structural formula 1 AO1.1 ALLOW structure/displayed/skeletal formula

IGNORE same molecular formula

Reference to E/Z isomerism or optical isomerism is

H 3C CH(CH3 )2 H CH(CH3 )2 ALLOW one mark if cis AND trans isomers of

cis isomer trans isomer

ALLOW one mark for correct identification of cis

cis isomer trans isomer

For C2H5–, ALLOW CH3CH2–

For bond into paper accept:

DO NOT ALLOW a bond angle of 180°