Unfamiliar_mechanisms 2

1(a) Ethers are a homologous series of organic compounds containing the R−O−R functional group.
The structures and names of two ethers are shown in Fig. 4.1.
Draw the skeletal formula of the ether, 2-ethoxy-3-methylbutane.
[1]
© OCR 2024. You may photocopy this page. 1 of 47 Created in ExamBuilder

(b) Ethers can be prepared by nucleophilic substitution of haloalkanes with alkoxide ions, RO−.
(i) Alkoxide ions can be prepared by reacting sodium with an alcohol. A gas is also formed.
Write an equation for the formation of methoxide ions from sodium and an alcohol.
[1]
(ii) Methoxyethane, shown in Fig. 4.1, can be prepared by reacting bromoethane, CH3CH2Br, with methoxide
ions, CH3O−.
Suggest the mechanism for the nucleophilic substitution of CH3CH2Br with CH3O−.
Show curly arrows, charges, relevant dipoles, and products.
[3]
(iii) In this mechanism, explain how CH3O− ions have acted as a nucleophile.
State the type of bond fission that takes place.
[1]
(c) 2-Ethoxypropane, shown in Fig. 4.1, is analysed by 1H NMR spectroscopy.
Complete the table to predict the 1H NMR spectrum of 2-ethoxypropane.
You may not need to use all the rows.
Chemical shift, δ/ppm Relative peak area Splitting pattern
[4]

(d) In organic reactions, alkoxide ions can also act as a base.
The diagram below shows an incomplete mechanism for the reaction of a diester with methoxide ions, CH3O−
(Step 1), followed by reaction of the intermediate with bromoethane (Step 2).
(i) For Step 1, add curly arrows to show how CH3O− reacts with the diester to form the intermediate.
In the box, draw the structure of the organic product formed in Step 2.
[3]
(ii) Explain how CH3O− ions have acted as a base in this mechanism.
[1]
2(a) Lactic acid is a naturally occurring chemical, which can be synthesised from ethanal, CH3CHO, as shown in the
steps below.
(i) Draw the structure for compound E.
[1]
(ii) Suggest a reagent that could be used for Step 2.

[1]
(iii) The displayed formula of lactic acid is shown below.
Suggest a value for each bond angle a–c.
Bond angle a: _ _ _ _ _ _ _ _ _
Bond angle b: _ _ _ _ _ _ _ _ _
Bond angle c: _ _ _ _ _ _ _ _ _
[2]
(b) Methyl lactate is an ester of lactic acid which is used as a solvent.
Methyl lactate can be hydrolysed by refluxing with sodium hydroxide solution.
In this reaction the hydroxide ion acts as a nucleophile.
(i) Suggest how the hydroxide ion can act as a nucleophile.
[1]
(ii) Part of the mechanism for the hydrolysis is shown below.

Add relevant dipoles and curly arrows to show how the intermediate is formed in Step 1 of the
mechanism.
Add curly arrows to show how the carboxylic acid and –OCH3 ion are formed from the intermediate in
Step 2 of the mechanism.
[4]
(iii) Methyl lactate can also react with ethanoyl chloride.
Complete the equation for this reaction.
[2]

3 * Methylcinnamaldehyde reacts with iodine monochloride, ICl, by electrophilic addition. The reaction produces a
mixture containing two different organic products.
The electronegativity values of chlorine and iodine are given in the table below.
Pauling electronegativity value

Cl 3.0
I 2.5
Outline the mechanism, using the ‘curly arrow’ model, for the formation of one of the organic products and
explain which of the two possible organic products is more likely to be formed.
In your mechanism, you can show the phenyl group as C6H5. [6]

4 This question is about two compounds used in medicine.
Cis-platin, PtCl2(NH3)2, is a complex of platinum which is used in cancer treatment.
(i) What is the oxidation number of platinum in cis-platin?
[1]
(ii) Cis-platin is prepared in a ligand substitution reaction which takes place in multiple steps.
The equation for the final step forming cis-platin is shown below.
[PtCl3(NH3)]− + NH3 → PtCl2(NH3)2 + Cl−

cis-platin
In the box, outline the mechanism for the formation of cis-platin from [PtCl3(NH3)]−.
Use curly arrows and lone pairs where appropriate.
[2]

5(a) This question is about reaction mechanisms.
Chemists use curly arrows in reaction mechanisms.
(i) What does a curly arrow show in a reaction mechanism?
[1]
(ii) Draw structures to show the products in the reaction mechanism below.
[2]
(iii) Use the mechanism in (ii) to explain what is meant by heterolytic fission.
[2]

(b) An incomplete reaction mechanism is shown below.
(i) Complete the mechanism by adding curly arrows and any missing species.
[4]
(ii) What is the role of OH– in this mechanism?
[1]
6 This question is about two different types of acid found in organic compounds, carboxylic acids and sulfonic
acids, as shown in Fig. 6.1.
Carboxylic acid Sulfonic acid
Fig. 6.1
Carboxylic acids and sulfonic acids both form esters.
Sulfonic acid esters can be hydrolysed by aqueous alkali.

The equation shows the alkaline hydrolysis of a sulfonic acid ester.
CH3SO2OCH3 + OH– → CH3SO2O– + CH3OH
In the 3 boxes below, add curly arrows to show the mechanism for this reaction.
In the first box, the hydroxide ion acts as a nucleophile.
[2]
7 ‘Diels-Alder’ reactions are used in the synthesis of many important organic compounds.

The Diels-Alder reaction of buta-1,3-diene with ethene is shown below.
(i) Add curly arrows to the diagram below to complete the mechanism for this Diels-Alder reaction.
[2]
(ii) Two more Diels-Alder reactions of buta-1,3-diene are shown below.
In the boxes, draw the organic product of each reaction.
[2]

8 This question is about reactions of phenol.
Salicylic acid can be prepared from phenol as shown below.
(i) Complete the mechanism below for Stage 1 and Stage 2.
Show curly arrows, the structure of the intermediate and the missing formulae on the dotted lines.
Stage 1
Stage 2
[6]

(ii) What are the roles of –OH and CO2 in the mechanism?
–
OH
CO2 [2]
(iii) Two molecules of salicylic acid can react together in the presence of an acid catalyst to form compound B.
Compound B has three rings and a molecular formula of C14H8O4.
Write the equation for this reaction showing the structures of organic compounds.
[3]

9 Vitamin C, C6H8O6, is a weak acid (Ka = 7.94 × 10 -5 (mol dm-3)), which is often referred to as ascorbic acid.
(i) In aqueous solution, vitamin C donates a proton to water:
C6H8O6 + H2O ⇌ C6H7O6 - + H3O+
Add curly arrows to the diagram to suggest the mechanism for this process.
[2]
(ii) The student dissolves 0.150 mol of vitamin C in water and makes the solution up to 250 cm3 in a volumetric
flask.
Calculate the pH of this solution of vitamin C.
Give your answer to 2 decimal places.
pH = ......................................................... [3]

10 ‘Ozonolysis’ is used in organic synthesis. Ozone breaks C=C bonds to form carbonyl compounds.
For example, the complete ozonolysis of methylbut-2-ene is shown below.
(i) Draw the structures of the products you would expect from the ozonolysis of the two compounds below.
[2]
(ii) The mechanism for ozonolysis takes place in several steps.
The curly arrows in the first step in the ozonolysis of methylbut-2-ene are shown below.
In the box, draw the structure(s) for the product(s) of this step.

[1]
11 Butan-1-ol reacts with sodium bromide and sulfuric acid to form 1-bromobutane by nucleophilic substitution.
The mechanism for this reaction takes place by two steps.
Step 1 The oxygen atom of the alcohol group accepts a proton to form a positively- charged intermediate.
Step 2 Bromide ions react with the intermediate from Step 1 by nucleophilic substitution to form
1-bromobutane.
Show both steps in this mechanism.
[4]
12 The benzenediazonium ion, shown below, is stable at temperatures below 10 °C.
Above 10 °C, the benzenediazonium ion reacts with water to form phenol.
The reaction proceeds in a three-step mechanism.

Step 1 Elimination of nitrogen gas to form a carbocation.
Step 2 Nucleophilic attack by water.
Step 3 Proton loss to form the organic product.
Complete the boxes below with intermediates and curly arrows to show the mechanism for this reaction.
[4]
END OF QUESTION PAPER

Mark Scheme
Question Answer/Indicative content Marks Guidance
1 a ✔ 1
b i 2Na + 2CH3OH → 2Na+ + 2CH3O– + H2 ✔ 1 ALLOW 2Na + 2CH3OH → 2CH3ONa + H2
ii 3 ALLOW correct structural OR skeletal OR

displayed formula OR mixture of the above
as long as non-ambiguous.
The curly arrow must start from O atom of

CH3O–
Curly arrow from CH3O– to carbon atom of AND must start either from a lone pair or
C-Br bond ✔ from the negative charge.
Dipole shown on C–Br bond, Cδ+ and Brδ– No need to show lone pair if curly arrow
AND curly arrow from C–Br bond to the Br comes from negative charge.
atom ✔
ALLOW SN1
Products of reaction (must not be Dipole shown on C–Br bond, Cδ+ and Brδ–,
ambiguous) ✔ and curly arrow from C–Br bond to the Br
atom.
Correct carbocation drawn.
AND curly arrow from CH3O– to
carbocation.
The curly arrow must start from the oxygen
atom of the CH3O–, and must start either
from a lone pair or from the negative
charge.
iii CH3O– donates an electron pair 1 ASSUME ‘it’ refers to CH3O–

AND heterolytic fission ✔
c Chemical Relative Splitting 4 ALLOW δ values ± 0.2 ppm, as a range or

shift, peak area pattern a value within the range
δ/ppm
0.5–1.9 3 Triplet ✔
3.0–4.3 2 Quartet ✔
0.5–1.9 6 Doublet ✔
3.0–4.3 1 Heptet ✔ ALLOW multiplet for heptet

Mark Scheme
d i 3
The curly arrow must start from O atom of

CH3O–
AND must start either from a lone pair or
from the negative charge.
No need to show lone pair if curly arrow

comes from negative charge.
Curly arrow from CH3O– to H of CH2 ✔

Curly arrow from C–H bond to C of CH2 ✔
ALLOW any unambiguous structure,

skeletal, displayed, structural or
combination.
ii CH3O– accepted a proton ✔ 1 ASSUME ‘it’ refers to CH3O–
Total 14

Mark Scheme
2 a i 1 ALLOW any combination of skeletal OR

structural OR displayed formula as long as
unambiguous
ii 1
aqueous acid OR H+ / H2O ALLOW H+(aq) / H2SO4(aq) / HCl(aq)
iii Angle a = 109.5° 2 ALLOW 109–110°
Angle b = 104.5° ALLOW 104–105°
Angle c = 120°
Two correct
All three correct
b i It is an electron pair donor OR donates a 1

lone pair

Mark Scheme
ii 4
Curly arrow must come from lone pair on O

Curly arrow from HO– to carbon atom of of HO– OR OH– OR from minus sign on
C=O bond HO– ion (No need to show lone pair if curly
arrow came from negative charge on O)
Correct dipole AND curly arrow from C=O
bond to Oδ–
____________________________
IGNORE dipole on C–O single bond
Curly arrow must come from lone pair on O

OR from minus sign on O– ion
Curly arrow from negative charge on
(No need to show lone pair if curly arrow
oxygen to C–O bond (to reform carbonyl π-
came from negative charge on O)
bond)
Curly arrow from C–O single bond to

oxygen atom (to form methoxide ion)
iii 2 ALLOW any combination of skeletal OR

Correct organic product: structural OR displayed formula as long as
unambiguous
HCl
Total 11

Mark Scheme
3 Please refer to marking instructions on 6 Please check all of page 23 which is

page 5 of mark scheme for guidance on included with this response. If this page is
how to mark this question. blank please annotate with SEEN
Level 3 (5–6 marks) Throughout: ALLOW correct structural OR

An outline of the mechanism for the displayed OR skeletal formulae OR a
formation of either product which is mostly combination of above if unambiguous
correct.
AND Indicative scientific points:
Major and minor products identified with a
correct explanation of which product is Mechanism for formation of either product.
most/least likely to be formed.
Curly arrow from C=C to attack the I
There is a well-developed line of reasoning atom of the I-Cl
which is clear and logically structured. The Correct dipole on I-Cl
information presented is relevant and Curly arrow from I-Cl bond to Cl
substantiated. Carbocation with full positive charge on
carbon atom
Level 2 (3–4 marks) Curly arrow from negative charge on
An outline of the mechanism for the Cl– or lone pair on Cl– to carbon atom
formation of either product but with a few with positive charge
omissions/errors.
AND Identifies major/minor product
correctly OR Explanation of which product
is most/least likely to be formed.
There is a line of reasoning presented with

some structure. The information presented
is relevant and supported by some
evidence.
OR
Level 1 (1–2 marks)
A basic outline of the mechanism for the
formation of either product is attempted.
OR
Basic explanation of which of the products
is most/least likely to be formed.
There is an attempt at a logical structure Organic products

with a line of reasoning.
The information is in the most part Major/most likely product
relevant.
0 marks
No response or no response worthy of
credit.
Minor/least likely product

Mark Scheme
Major/most likely product is formed

from the most stable carbocation
intermediate OR – Cl is attached to
carbon atom with the least hydrogens
attached OR the carbon with the most
–C atoms attached OR the – I is
attached to the carbon atom with most
hydrogens attached
Examiner’s Comments
This question was marked using a level of

response mark scheme. Most candidates
gave an answer worthy of at least level two
(3-4 marks) by providing a suitable
mechanism and identifying the major
product. The strongest candidates
identified both products and were able to
describe which was most likely. Such
responses received level 3 (5-6 marks) as
shown in Exemplar 9. Lower ability
candidate responses seemed to ignore the
reference to electrophilic addition in the
question and tried reacting ICl with either
the benzene ring or the aldehyde group.

Mark Scheme
Exemplar 9
This response starts with a clear outline of

the electrophilic addition mechanism
showing correct partial charges and
accurately drawn curly arrows. The
structures of the two possible organic
products are shown and the most likely
product to be formed is identified correctly.
Notice that the candidate has labelled
these structures as ‘Product A’ and
‘Product B’ and refers to the labels later in
the response. This is a good strategy,
which enables the candidate to provide a
clear and easy to follow answer. The
response concludes with a detailed
explanation, referring to carbocation
stability to justify why product A is most
likely to be formed. This response
therefore satisfies the Level 3 criteria. The
response is logically structured with a well-
developed line of reasoning and was
therefore credited the upper mark within
the level and achieved six marks.
Total 6

Mark Scheme
4 i +2 1 ALLOW 2+ OR +II
Sign required ALLOW Pt2+
Almost all candidates responded with the

correct oxidation number of +2. Incorrect
responses were 0 (the overall charge of
the complex), +4 or 2 (with no sign).
Candidates are reminded on the

importance of the sign in assigning
oxidation numbers.
ii 2 For [PtCl3(NH3)]– :
• IGNORE dipoles
• IGNORE absence of – charge
• IGNORE – charge shown on atoms
ALLOW any 4 coordinate shape for

Curly arrow from lone pair on NH3 to Pt ✓ [PtCl3(NH3)]–,
|
[PtCl3(NH3)]– drawn with 1 Pt, 3 Cls and 1 e.g. tetrahedral;
NH3
AND
Curly arrow from any Pt Cl bond in the 1st curly arrow must
complex ✓ •go to Pt
AND
start from, OR be traced back to any
ALLOW SN1 mechanism: point across width of lone pair on N of
NH3
DO NOT ALLOW charge on NH3

nucleophile, e.g. NH3–
Mark curly arrows as above for SN2 2nd curly arrow must start from, OR be
Requires + on platinum intermediate traced back to, any part of Pt–Cl bond and
go to one of the 3 Cl atoms

Mark Scheme
This part required candidates to apply their

knowledge and understanding of the
nucleophilic substitution mechanism in a
novel context.
This part discriminated extremely well with

able candidates drawing the correct initial
complex and showing precisely positioned
curly arrows, dipoles and the role of the
NH3 lone pair, as shown in Exemplar 7.
Lower ability candidates often showed

imprecise curly arrows or placed a
negative charge on NH3, as shown in
Exemplar 8.
Exemplar 7
Exemplar 8
Total 3

Mark Scheme
5 a i Movement of an electron pair ✓ 1 (AO For electron pair,

1.1) ALLOW lone pair OR bonding pair OR 2
electrons
Most candidates were able to state that a

curly arrow shows the movement of a pair
of electrons. However, many candidates
gave responses that lacked precision, such
as ‘movement of electrons’. Such
responses did not receive credit as the
number of electrons was not specified.
ii 2(AO 3.1 ALLOW any combination of skeletal OR

×2) structural
OR displayed formula as long as
unambiguous
Correct carbon skeleton ✓
IGNORE any other products
‘+’ charge on correct carbon skeleton ✓
This demanding question required

candidates to apply their knowledge of
curly arrows to an unfamiliar intermediate.
Examiners were impressed by the number
of good responses and many candidates
were able to draw an organic product with
the correct carbon skeleton. The best
responses demonstrated candidates’ flair
for the subject and these recognised that a
carbocation would be formed rather than
an alkane.

Mark Scheme
iii Heterolytic 2(AO ALLOW 2 electrons go to one (bonded)

one (bonded) atom/O receives both/2 1.2)(AO atom/O
electrons ✓ 1.1)
IGNORE formation of ions/radicals
Fission
Breaking of a covalent bond For O atom,
OR breaking of C-O bond ✓ ALLOW species
DO NOT ALLOW element OR molecule
‘Bond breaking’ is not sufficient

(no reference to covalent)
Many candidates were able to describe the

meaning of ‘heterolytic’, referring to both
electrons going to the O atom. However,
only some candidates described ‘fission’
and a significant proportion of these
referred only to ‘bond breaking’. The best
responses correctly stated that fission is
the breaking of a covalent bond. Candidate
are encouraged to read questions carefully
and take notice of words that appear in
bold type as these often communicate
what is expected in a question.

Mark Scheme
b i 4 (AO 3.2 IGNORE any dipoles shown

×4)
NOTE: curly arrows can be straight, snake-
like, etc.
but NOT double headed or half headed
arrows
Curly arrow from OH– must
go to the C of C=O
AND

point across width of lone pair on O of
OH–
OR start from – charge–OH ion
Curly arrow from C=O bond must start

from, OR be traced back to, any part of
C=O bond and go to O
Curly arrow from O–must
go to C=O bond
AND
start from, OR be traced back to, any

point across width of lone pair

Mark Scheme
OR start from ‘–‘ charge of O–
Curly arrow from C–Cl bond must start

C–Cl bond and go to Cl
Examiners were encouraged by the

number of excellent responses to this
question. Candidates were able to
confidently apply their knowledge of
mechanisms to this unfamiliar example and
the majority of the cohort scored at least
two marks. In the first step candidates
used their understanding of nucleophilic
addition to show a correct curly arrow from
the hydroxide ion to the C of the C=O bond
as well as an arrow from this bond to the
O. Many candidates were able to show the
breaking of the C–Cl bond and the
formation of a chloride ion, drawing on their
experience of the reactions of haloalkanes.
Some candidates recognised the need to
include an arrow to reform the carbon-
oxygen double bond, with the best
responses showing this accurately. A
common error was to draw the bond from

Mark Scheme
the lone pair on O to the C atom, rather

than the bond.
ii (OH–) donates an electron pair/lone pair 1(AO 1.2)

OR (OH– acts as a) nucleophile ✓
Total 10

Mark Scheme
6 4 IGNORE any added charges OR dipoles.

(AO Marks solely for curly arrows
3.1×4)
6 curly arrows correct ✓✓✓✓

5 curly arrows correct ✓✓✓ IGNORE any curly arrows on bottom
4 curly arrows correct ✓✓ structures (not in boxes):
3 curly arrows correct ✓
Most candidates showed a good

understanding and appreciation of drawing
curly arrows. It must be stressed that curly
arrows that do not start from a lone pair,
negative charge or a bond cannot be
credited.
Lower-attaining candidates often drew

imprecisely positioned curly arrows, curly
arrows in the wrong direction or to the
wrong atoms.
For their response to be credited with

marks, candidates should position curly
arrows to ensure credit when outlining
reaction mechanisms.
Total 4

Mark Scheme
7 i 2 IGNORE any dipoles shown

(AO2.5×2
) NOTE: curly arrows can be straight, snake-
like, etc.
but NOT half headed or double headed
1 mark for each curly arrow ✓✓ arrows
Curly arrow from C=C bond must

start from, OR be traced back to,
Lower left: any part of C=C bond and go to
C–C
Upper left: any part of C=C bond and go to
gap between C=C and C=C
Many candidates did not apply their

knowledge of curly arrows to this unfamiliar
context. Those that scored a mark often
did so for the top curly arrow but missed
the requirement of the second curly arrow.
ii 2 Examiner’s Comments
(AO3.2×2
) Many candidates did not correctly answer
this question with products being given that
had too few carbon atoms.
Total 4

Mark Scheme
8 i Stage 1 6 (AO1.1) ANNOTATE WITH TICKS AND CROSSES

(AO1.2)
(AO2.5) NOTE: curly arrows can be straight, snake-
(AO2.5) like, etc.
(AO2.5) but NOT double headed or half headed
1 mark for each curly arrow as shown. (AO1.2) arrows
Stage 2 Curly arrow from OH– must
Curly arrow from π-ring to C in CO2 go to the H of O–H

AND AND
curly arrow from the C=O bond to O atom start from, OR be traced back to any
✓ point across width of lone pair on O of
OH–
OR start from – charge–OH ion
Correct intermediate ✓ Curly arrow from

C–H bond to reform π-ring
AND H+ formed ✓
Curly arrow from O–H bond must start

O–H bond and go to O
IGNORE dipoles on O-H bond
IGNORE Na+
1st curly arrow must
go to the C of CO2
AND
start from, OR close to circle of
benzene ring
2nd curly arrow must start from, OR be

traced back to, any part of C=O bond and
go to O

Mark Scheme
ALLOW 2nd curly arrow from C=O to any

O in CO2
DO NOT ALLOW the following

intermediate:
π-ring must cover more

than half of the benzene ring structure
AND
the correct orientation, i.e. gap towards C
with CO2–
ALLOW + sign anywhere inside the

‘hexagon’ of the intermediate.
DO NOT ALLOW mark for intermediate if

phenolic O– is missing
curly arrow must start from, OR be traced

back to, any part of C-H bond and go
inside the ‘hexagon’
Candidates who answered this question

well had clear mechanisms. Too often
positioning of curly arrows was ambiguous.

Mark Scheme
ii OH– : base ✓ 2 ALLOW alkali

(AO2.1×2 IGNORE ‘nucleophile’, ‘donates electron
CO2: electrophile OR electron pair ) pair’
acceptor ✓
IGNORE lone pair acceptor (No lone pair
involved)
iii 3 (AO3.1) Examiner’s Comments

(AO3.2)
(AO2.6) Candidates who found this question
difficult often did not recognise the
functional groups present in the reacting
molecule. Those that identified an
esterification reaction often then did not
One ester link in organic product ✓
balance the equation.
Correct structure of organic product ✓
Correct equation AND balanced ✓
Total 11

Mark Scheme
9 i 2 IGNORE incorrect curly arrows IGNORE

(2 ‘double’ curly arrows such as:
×AO3.2)
3 OR 4 curly arrows correct → 2 marks ✓ ✓

1 curly arrow correct → 1 mark ✓
H2O Curly arrow must

point across width of lone pair on H2O:
This novel mechanism assessed a

candidate’s understanding of curly arrows,
and four curly arrows were needed. One
mark was available for one correct curly
arrow, usually from the H2O: or from the
C=O. 2 marks were given for three or four
correct curly arrows. The two curly arrows
within the ring structure proved to be the
most difficult. The question discriminated
extremely well: many candidates were able
to secure one mark with the most able
being given both marks. A candidate
showing all four curly arrows correctly
demonstrated an excellent understanding
of curly arrows.

Mark Scheme
ii FIRST CHECK ANSWER ON THE 3 For [H+]

ANSWER LINE (2 ALLOW ECF from incorrect [vitamin C]
If answer = 2.16 award 3 marks ×AO2.4) for pH
(1 ALLOW ECF ONLY if [H+] has been
--------------------------------------------------------- ×AO1.2) derived from Ka AND [vitamin C]
[Vitamin C] = 0.150 × 4 = 0.600 (mol dm-3) ---------------------------------------------------------
✓ COMMON ERRORS
0.6 seen anywhere pH = 4.32 2/3 calculation marks
[H+] = √ (Ka × [Vitamin C]) No square root of (7.94 × 10-5 × 0.600)
= √ (7.94 × 10-5 × 0.600) pH = 2.46 2/3 calculation marks
= 6.90 × 10-3 (mol dm-3) ✓ No ×2 4 (7.94 × 10-5 × 0.150)
pH = -log [H+] pH = 2.76 2/3 calculation marks
= -log 6.90 × 10-3 ÷ 4 (7.94 × 10-5 × 0.0375)
= 2.16 ✓ pH = 4.92 1/3 calculation mark
2 DP required No square root AND 0.150
pH = 5.53 1/3 calculation mark
No square root AND 0.0375
Most candidates had learnt a standard

method for calculating the pH of a weak
acid. with the correct answer of 2.16 being
seen on very many scripts. Success
required conversion of 0.150 moles of
vitamin C in 250 cm3 to its concentration as
0.600 mol-3, calculation of [H+] using [H+] =
√ (Ka × [HA]) and determination of pH
using -log[H+].
Common errors usually resulted from one

mistake and could still be rewarded with 2
of the available 3 marks. Examples are
shown below.
pH = 4.32 No square root of (7.94 ×

10-5 × 0.600)
pH = 2.46 No conversion of 0.150 mol
to 0.600 mol dm-3 → (7.94 × 10-5 ×
0.150)
pH = 2.76 ÷ 4 instead of × 4 for
concentration → (7.94 × 10-5 × 0.0375)
AfL
pH calculations are common in A Level

Chemistry

Mark Scheme
There are four different types, and it is

essential that the standard methods for
determination of [H+] in the calculations are
learnt:
pH of strong acids
pH of weak acids, using Ka and [HA]
pH of strong bases, using Kw and
[OH-]
pH of buffers, using Ka and [HA]/[A-]
It is extremely likely that at least one of

these types of pH calculation will feature in
at least one of the A Level units.
Total 5

Mark Scheme
10 i 2 ALLOW any combination of skeletal OR

(AO3.1×1 structural OR displayed formula as long as
) unambiguous
(AO3.2×1
BOTH structures required for ✓
)
ii 1 ALLOW any combination of skeletal OR

(AO3.2) structural OR displayed formula as long as
unambiguous
Most candidates were able to score 1 mark

for correctly drawing the structures of the
two aldehyde products of the first reaction.
The second reaction proved more
challenging, with most candidates
incorrectly drawing two products.
Few candidates were given this mark. A

common error was to produce multiple
products (rather than a ring structure) or to
put positive/negative charges on the
oxygen atoms within the ring structure.
Total 3

Mark Scheme
11 Step 1 The oxygen atom of the alcohol 4 (AO3.2 ALLOW any combination of skeletal OR
group accepts a proton to form a positively- ×4) structural OR displayed formula as long as
charged intermediate. unambiguous
For CH3CH2CH2, ALLOW CH3(CH2)2, C3H7
2 marks IGNORE dipoles
------------------------------------------------
ALLOW curly arrow to
H of H-O-SO3H OR H-Br
IGNORE absence of curly arrow from H-O
or from H-Br
+ charge MUST be on O of intermediate
Step 2 Bromide ions react with the Curly arrow must
intermediate by nucleophilic substitution to
form 1-bromobutane. start from, OR be traced back to any
point across width of lone pair on :Br-
2 marks OR :OH OR start from - charge on Br-
2 possible routes: (Lone pair NOT needed if curly arrow

EITHER shown from - charge on Br-)
IGNORE final products:
1-bromobutane and H2O
IF C3H7CH2-O+H2 is not shown,
ALLOW intermediate mark for carbocation:
C3H7CH2+
ALLOW 2 marks max for mechanism
OR without positively charge intermediate, i.e.
If in doubt, contact Team Leader
This question is one of two on this paper

assessing understanding of unfamiliar
organic reaction mechanisms. The stem to
the question includes important information
and clues that should have then guided
candidates towards this unfamiliar
mechanism (which is related to the familiar
nucleophilic substitution of haloalkanes).
The two prompts for Step 1 and Step 2 are
critical but many candidates did not use
these, instead inventing their own
mechanisms. However, there were many
successful responses seen that gained the

Mark Scheme
full 4 marks.
Exemplar 2
Exemplar 2 illustrates a limited

appreciation of what curly arrows mean
and the importance of charges and dipoles.
Step 1 is an attempt to show the alcohol
OH group accepting a proton, but a curly
arrow shows the movement of an electron
pair. It cannot travel from a + charge to a
lone pair. The intermediate shown does
contain the correct atoms but the + charge
has been omitted from the O atom.
Marks were given for the curly arrow from

the Br- lone pair and from the C-O bond.
However, the candidate has drawn the
bonds with very short lines making it all too
easy for a curly arrow to be shown
imprecisely. This response was given 2/4
marks.
Assessment for learning
In organic chemistry mechanisms, a curly

pair and demonstrates the direction of
electron flow in organic reactions.
A curly arrow must start from:
A lone pair or negative charge and go

to an atom to show where a bond
forms
A bond to show where a bond breaks.
In Q3b, curly arrows start
from a lone pair on the alcohol OH and

a Br- ion
from a C-O bond

Mark Scheme
A curly arrow will not originate from a +

charge.
Total 4

Mark Scheme
12 Mechanism: 4 ANNOTATE ANSWER TICKS AND

(AO 3.2 CROSSES
×4) --------------------------------------------------
NOTE: Curly arrows can be straight, snake-
like, etc. but NOT half arrows
1st curly arrow must start from, OR be

traced back to, any part of C–N+ bond and
go to N OR + of N+
M1: Curly arrow from C–N bond to N+

✓
M2: AND N2 ✓ 2nd curly arrow must

M3: Curly arrow from lone pair of O of
point across width of lone pair on O of
H2O to C+ ✓
H2O
go to the C or + of C+ of C6H5+
M4 AND Curly arrow from
O–H bond to O+ ✓
For all marks, treat additional curly

arrows as CON
3rd curly arrow must
ALLOW M3 shown in bottom box
start from ‘–‘ of O–H of –OH2+
IGNORE partial charges go to O or + of O+
ALLOW M3 AND M4 combined
e.g.
--------------------------------------------------
For DO NOT ALLOW M2
for carbocation
BUT
For DO NOT ALLOW M2 for
ALLOW for M3 and/or M4 by ECF,
carbocation
BUT e.g.
ALLOW for M3 and/or M4 by ECF,
e.g.

Mark Scheme
This question required candidates to apply

their understanding of organic mechanisms
to an unfamiliar reaction. The stem to the
question includes important information
and clues that should have guided
candidates towards this unfamiliar
mechanism, with the prompts for the three
steps being critical. Many responses fell
back to the familiar mechanism for
electrophilic substitution, an approach that
could not be credited.
This question discriminated very well but

many candidates scored few marks.
Exemplar 1
This response has been included to show

a candidate with an excellent
understanding of the meaning of curly
arrows and the importance of charges and
dipoles. The prompts in the question are
followed and the candidate has been given
all four marks.
Notice how the curly arrows start either

from a bond or from a lone pair. The
candidate has also realised that the
addition of H2O produces a positively
charged oxonium ion. Many candidates
omitted the ‘+’ charge or showed the curly
arrow for loss of a proton going to a H
atom rather than the O atom of water.

Mark Scheme
Assessment for learning
In organic chemistry mechanisms, a curly

pair and demonstrates the direction of
electron flow in organic reactions.
A curly arrow must start from:
A lone pair or negative charge and go

to an atom to show where a bond
forms
A bond to show where a bond breaks.
In Question 2 (c), curly arrows:
start from a C–N bond to form the

intermediate carbocation by elimination
of N2
go from a lone pair on the water O
atom to the + charge of the carbocation
go from an O–H bond to the + charge
on the oxonium ion, losing a proton H+
in the process.
Total 4
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1(a) Ethers are a homologous series of organic compounds containing the R−O−R functional group.

Draw the skeletal formula of the ether, 2-ethoxy-3-methylbutane.

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Show curly arrows, charges, relevant dipoles, and products.

State the type of bond fission that takes place.

(c) 2-Ethoxypropane, shown in Fig. 4.1, is analysed by 1H NMR spectroscopy.

Complete the table to predict the 1H NMR spectrum of 2-ethoxypropane.

You may not need to use all the rows.

Chemical shift, δ/ppm Relative peak area Splitting pattern

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(i) Draw the structure for compound E.

(ii) Suggest a reagent that could be used for Step 2.

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(iii) The displayed formula of lactic acid is shown below.

Suggest a value for each bond angle a–c.

(b) Methyl lactate is an ester of lactic acid which is used as a solvent.

Methyl lactate can be hydrolysed by refluxing with sodium hydroxide solution.

In this reaction the hydroxide ion acts as a nucleophile.

(i) Suggest how the hydroxide ion can act as a nucleophile.

(ii) Part of the mechanism for the hydrolysis is shown below.

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(iii) Methyl lactate can also react with ethanoyl chloride.

Complete the equation for this reaction.

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Pauling electronegativity value

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Cis-platin, PtCl2(NH3)2, is a complex of platinum which is used in cancer treatment.

(i) What is the oxidation number of platinum in cis-platin?

[PtCl3(NH3)]− + NH3 → PtCl2(NH3)2 + Cl−

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Chemists use curly arrows in reaction mechanisms.

(i) What does a curly arrow show in a reaction mechanism?

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(ii) What is the role of OH– in this mechanism?

Carboxylic acid Sulfonic acid

Sulfonic acid esters can be hydrolysed by aqueous alkali.

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CH3SO2OCH3 + OH– → CH3SO2O– + CH3OH

In the first box, the hydroxide ion acts as a nucleophile.

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(ii) Two more Diels-Alder reactions of buta-1,3-diene are shown below.

In the boxes, draw the organic product of each reaction.

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Salicylic acid can be prepared from phenol as shown below.

(i) Complete the mechanism below for Stage 1 and Stage 2.

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Compound B has three rings and a molecular formula of C14H8O4.

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(i) In aqueous solution, vitamin C donates a proton to water:

C6H8O6 + H2O ⇌ C6H7O6 - + H3O+

Calculate the pH of this solution of vitamin C.

Give your answer to 2 decimal places.

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For example, the complete ozonolysis of methylbut-2-ene is shown below.

(ii) The mechanism for ozonolysis takes place in several steps.

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The mechanism for this reaction takes place by two steps.

Show both steps in this mechanism.