25 Aromatic chemistry

OCR Chemistry A Exam-style mark scheme

Question
Answer Marks Guidance
number
1a 3 electrons from each C used to form (σ)-bonds B1 Marks can be scored from suitable
to 2C and an H atom labelled diagram (words in bold need
to be included)
1 electron from each C atom/electron in a B1
p-orbital overlaps with electrons from adjacent
C atoms/electrons in p-orbitals

Create delocalised system of electrons B1

Rings of charge / -bonds above and below B1

plane of C atoms
1bi Contains alternating double and single bonds B1 ALLOW: 3 separate double bonds /

m
3 separate -bonds

er as
1 b ii Benzene is less reactive than predicted (by B1

co
Kekulé structure)

eH w
o.
CC bond lengths in benzene are all same length
rs e B1 ALLOW intermediate in length
between that of single and double
ou urc
bond
Enthalpy change of hydrogenation is less B1
negative than predicted (by Kekulé structure)
ALLOW enthalpy change is smaller /
less energy is released
o

2a phenol B1
aC s
v i y re

2b 1,3-dinitrobenzene B1 ALLOW without hyphen

2c 2-chloromethylbenzene B1 ALLOW 2-chloro-1-methylbenzene
IGNORE extra hyphens or gaps
ed d

3ai Concentrated nitric acid  concentrated B1 ALLOW concentrated nitric and

sulfuric acid sulfuric acid
ar stu

3 a ii CH3CCl(CH3)CH3 B1 ALLOW any combination of

full/skeletal/partial structural formula
3 a iii Temperature not above 50 °C B1
sh is
Th

Prevents further substitution/formation of B1

dinitrobenzene
3 a iv Friedel–Crafts B1 ALLOW minor errors of spelling e.g.
Freidel
3av Aluminium chloride B1 ALLOW iron (III) chloride/iron (III)
bromide

NOT iron alone

3bi Correct structure showing a tertbutyl group on C B1 ALLOW 2,4 or 2,4,6 isomer
atom 2
i.e. tertbutyl group at any other position
is CON

This©study
Oxford University
source Pressby2016
was downloaded http://www.oxfordsecondary.co.uk/acknowledgements
100000833708663 from CourseHero.com on 10-06-2021 01:17:46 GMT -05:00
This resource sheet may have been changed from the original 1
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 25 Aromatic chemistry
OCR Chemistry A Exam-style mark scheme

Question
Answer Marks Guidance
number

3 b ii The (tertbutyl) group will not be in the correct B1

position

The NO2 group directs substitution to 3,5 position B1 ACCEPT just 3-position
4 Level of response mark scheme: Ethanol will not give any positive
result
5–6 marks
It is not acidic

m
Gives correct set of observations for each

er as
substance Ethanoic acid will fizz with sodium

co
carbonate

eH w
AND
And will react with sodium hydroxide,

o.
Relates each observation correctly to the acidity
rs e causing indicator to turn
of the molecule red/orange/green
ou urc
AND Because ethanoic acid is strong
enough acid to react with both alkalis
Writes a correct equation for all three reactions and carbonates
o
aC s

3–4 marks CH3COOH  NaOH

 CH3COO−Na+  H2O
v i y re

Gives mostly correct observations but with some 2CH3COOH + Na2CO3

omissions and / or lack of clarity in the  2CH3COO−Na+  CO2  H2O
description
Phenol will not fizz with sodium
ed d

AND carbonate
ar stu

Relates most observations to the acidity of the But will react with sodium hydroxide,
molecule causing indicator to turn
red/orange/green
sh is

AND
C6H5OH  NaOH
Th

Writes 2 correct equations for all three reactions  C6H5O−Na+  H2O

1–2 marks

Gives limited number of correct of observations

AND

Relates some of these to the acidity of the

molecule but with some lack of accuracy

AND

Writes one correct equation

This©study
Oxford University
source Pressby2016
was downloaded http://www.oxfordsecondary.co.uk/acknowledgements
100000833708663 from CourseHero.com on 10-06-2021 01:17:46 GMT -05:00
This resource sheet may have been changed from the original 2
https://www.coursehero.com/file/72614755/25-Aromatic-Chemistry-MSdoc/
 25 Aromatic chemistry
OCR Chemistry A Exam-style mark scheme

Question
Answer Marks Guidance
number
5a Products of reaction ( 1 mark each):

B1

B1

If electrophilic missing from both

mechanisms, award 1 mark
B1

B1

m
er as
5bi Benzene  bromine: intermediate

co
eH w
o.
rs e
ou urc
1 mark: correct structure B1 ALLOW  charge on C atom 2 and 2
o

 double bonds between C atoms

34 and 56
aC s

1 mark: correct position of positive charge B1

v i y re

Cyclohexene  bromine
ed d
ar stu

1 mark: correct structure

sh is

1 mark: correct position of positive charge

Th

B1

B1
5 b ii Benzene and bromine:

C–H bond breaks AND electrons donated to ring B1 ACCEPT diagram showing correct
electron movement
Regenerates stable delocalised structure B1

Cyclohexene and bromine B1 ACCEPT diagram showing correct

electron movement

This©study
Oxford University
source Pressby2016
was downloaded http://www.oxfordsecondary.co.uk/acknowledgements
100000833708663 from CourseHero.com on 10-06-2021 01:17:46 GMT -05:00
This resource sheet may have been changed from the original 3
https://www.coursehero.com/file/72614755/25-Aromatic-Chemistry-MSdoc/
 25 Aromatic chemistry
OCR Chemistry A Exam-style mark scheme

Question
Answer Marks Guidance
number

Br- donates electron pair to carbocation ACCEPT no delocalisation to reform

B1
Carbocation is unstable / strongly attracts Br− ion

m
er as
co
eH w
o.
rs e
ou urc
o
aC s
v i y re
ed d
ar stu
sh is
Th

This©study
Oxford University
source Pressby2016
was downloaded http://www.oxfordsecondary.co.uk/acknowledgements
100000833708663 from CourseHero.com on 10-06-2021 01:17:46 GMT -05:00
This resource sheet may have been changed from the original 4
https://www.coursehero.com/file/72614755/25-Aromatic-Chemistry-MSdoc/
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