Aromatic Chemistry Questions

Answer all the questions.
1. Which of the following support(s) the delocalised model for benzene rather than the Kekulé model?
1: Benzene is less reactive than cyclohexene

2: A benzene molecule has a planar, hexagonal structure
3: The enthalpy change of hydrogenation of benzene is more exothermic than predicted from the Kekulé
structure
A 1, 2 and 3
B Only 1 and 2
C Only 2 and 3
D Only 1
Your answer
[1]
2. What is the mechanism for the nitration of benzene?
A Nucleophilic addition
B Nucleophilic substitution
C Electrophilic addition
D Electrophilic substitution
Your answer
[1]
3. A student adds bromine water to a solution of phenol.
What would the student see during this reaction?
A Bromine water goes from orange to green.

B Bromine water goes from orange to colourless and a white precipitate is formed.
C There is no reaction.
D Bromine water goes from orange to colourless and the solution fizzes.
Your answer
[1]
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4. Which reagent could be used to distinguish between CH3CH2OH and C6H5OH?
A AgNO3(aq) in ethanol
B CH3COCl
C Na2CO3(aq)
D Bromine water
Your answer
[1]

5. Bromine is reacted separately with nitrobenzene and phenylamine.
Which organic products are likely to form?
Your answer
[1]
6. Two chemical tests are carried out on an aqueous solution of an aromatic organic compound Y.
The results of the tests are shown below.
Test Br2(aq) Na2CO3(aq)

Observation decolourised effervescence
What is the minimum number of C atoms in Y?
A 6
B 7
C 8
D 9
Your answer
[1]

7. What is the number of sigma bonds in a benzene molecule?
A 3
B 6
C 9
D 12
Your answer
[1]

8(a). The chemist carries out further investigations into the reactions of substituted benzene compounds.
The table below shows the directing effects of different groups attached to a benzene ring.
Group Position to which new substituent is

directed
–NO2 3
–OH 2, 4
–COCH3 3
–N(CH3)2 2, 4
–NHCOCH3 2, 4
–CN 3
(i) Draw all of the organic products from monosubstitution reactions of the substituted benzene compounds
shown below.
[3]
(ii) The reactions of C6H5N(CH3)2 are similar to the reactions of phenol.

Draw the organic product that is formed from the tri-substitution of C6H5N(CH3)2 with chlorine.
[1]
(iii) Explain why chlorine reacts much more readily with C6H5N(CH3)2 than with benzene.
[3]

(b). This question is about the chemistry of benzene and substituted benzene compounds.
In 1865, the Kekulé model was suggested for the structure of benzene. Experimental evidence has led to the
development of an updated model. Both models are shown below.
Explain the experimental evidence that led to the development of the updated model from the Kekulé model
of benzene.
Describe the bonding in the updated model of benzene.
[4]

(c). A chemist investigates the chlorination of methylbenzene and finds that the methyl group has a 2– and 4–
directing effect.
4-Chloromethylbenzene is one of the products of the chlorination of methylbenzene.
Outline the mechanism for the formation of 4-chloromethylbenzene from methylbenzene and chlorine in the
presence of the catalyst, AlCl3.
Show how AlCl3 behaves as a catalyst.
[5]
9. Give chemical explanations for the following statements.
The carbon–carbon bonds in benzene are all the same length.
[1]

10. Chemists often use two different structures to represent a molecule of benzene, as shown below.
(i) Describe, with the aid of suitable diagrams showing orbital overlap, the difference in bonding between
structure A and structure B.
In your answer, you should use appropriate technical terms, spelled correctly.
[4]

(ii) The table below shows the enthalpy changes for the reactions of cyclohexene, C6H10, and benzene, C6H6,
with hydrogen.
reaction enthalpy change / kJ mol−1
C6H10 + H2→ C6H12 −119
C6H6 + 3H2→ C6H12 −208
Using this information, suggest and explain whether structure A or structure B is a better representation of
benzene.
[2]

11. A student analysed a mixture of compounds found in red wine using gas chromatography followed by mass
spectrometry (GC-MS).
Two of the compounds found to be present in the mixture are shown below.
1 mol of compound B reacts with 2 mol of bromine, Br2 by electrophilic substitution.
Write a balanced equation for this reaction, showing clearly the structure of the organic compound.
[1]

12(a). The organic compounds in the table below can be termed, aliphatic, alicyclic or aromatic.
Identify, using letters E, F, G, H, I, J, the compound(s) which are the following types.
Each response may contain more than one letter.
aliphatic _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
alicyclic _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
aromatic _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
[3]
(b). Compound I has one alkyl group.
What is the general formula of alkyl groups?
[1]
(c). Compound H can be prepared in an elimination reaction by heating compound J with an acid catalyst.
A student carries out this preparation using 7.65 g of compound J.
The student obtains 2.05 g of compound H.
(i) Write an equation for this reaction, using molecular formulae.

Calculate the percentage yield of compound H.
Give your answer to one decimal place.
percentage yield = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ % [4]
(ii) Describe a simple test that the student could carry out to confirm the presence of the functional group in
compound H.
Draw the structure of the organic product from the test.
test:
organic product =
[2]

13(a). This question is about medical compounds made from salicylic acid.
Salicylic acid can be made from the reaction of phenol with carbon dioxide as shown below.
(i) Stage 2 takes place by electrophilic substitution and part of the mechanism is shown below.
Complete the mechanism by showing relevant dipoles, curly arrows and the structure of the intermediate.
[3]
(ii) What type of reaction takes place during Stage 1 and Stage 3?

Explain your answer.
Type of reaction _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
Explanation _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _
[2]
(iii) A chemist prepares 4.83 g of salicylic acid from phenol. The percentage yield of this reaction is 45.0%.
Calculate the mass of phenol that the chemist uses.
Give your answer to three significant figures.
mass of phenol = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ g [3]

(b). Aspirin is an ester of salicylic acid.
Aspirin can be prepared by reacting salicylic acid with ethanoic anhydride, (CH3CO)2O. One other organic
compound also forms.
Draw skeletal formulae for the products of this reaction.
[2]

14(a). Salicylic acid is a naturally occurring carboxylic acid, widely used in organic synthesis.
The flowchart below shows some reactions of salicylic acid.
(i) In the box below, draw the structure of the organic compound formed by reaction 1.
[1]
(ii) Describe what would be observed during reaction 2.

[1]
(iii) Write a chemical equation to represent reaction 2.
[1]
(iv) State the reagents and conditions in reaction 3.
[1]

(b). Bromine reacts more readily with salicylic acid than with benzene.
(i) Outline the mechanism for the bromination of salicylic acid shown in reaction 2 in the flowchart.
A halogen carrier is not required for this reaction.
The electrophile is Br2.
[4]
(ii) Explain why bromine reacts more readily with salicylic acid than with benzene.
In your answer, you should use appropriate technical terms, spelled correctly.
[3]
END OF QUESTION PAPER

Mark Scheme
Question Answer/Indicative content Marks Guidance
1 D 1
Total 1
2 D 1
Total 1
3 B 1
Total 1
4 D 1
Total 1
5 C 1
Total 1
6 B 1
Total 1
7 D 1
Total 1
8 a i 3 IGNORE names throughout
DO NOT ALLOW poly-substituted

products
DO NOT ALLOW 2-chloro or 4-chloro

products
DO NOT ALLOW 3-chloro product

Mark Scheme
ii 1
iii (In C6H5N(CH3)2) 3 ALLOW diagram to show movement of

lone pair into ring but delocalised ring
must be mentioned
ALLOW lone pair of electrons on N is

(lone) pair of electrons on N is (partially) (partially) drawn / attracted / pulled into
delocalised into the ring delocalised ring
electron density increases / is higher (than DO NOT ALLOW charge density or

in benzene) ORA electronegativity
ALLOW Cl2 is (more) attracted

OR Cl2 is not polarised by benzene
OR induces dipoles (in chlorine /
Cl2 / electrophile is (more) polarised ORA electrophile)

Mark Scheme
b Experimental evidence – ANY TWO from 4
carbon–carbon bond lengths are the same

in benzene
Enthalpy change of hydrogenation is less

(exothermic) for benzene (than for Kekulé
model)
Discussion of named reaction to highlight

greater stability, e.g. chlorination of
benzene requires a catalyst whereas no
catalyst is needed for alkenes
Bonding in modern model
p-orbitals overlap to form π bonds ALLOW both marks for correctly labelled
diagrams showing overlap of p-orbitals to
(π–)electrons are delocalised form delocalised π–electrons

Mark Scheme
c Generation of electrophile 5 ANNOTATE ANSWER WITH TICKS AND

AlCl3 + Cl2 → AlCl4–+ Cl+ CROSSES
Electrophilic substitution
Curly arrow from π-bond to Cl+ DO NOT ALLOW the following

intermediate:
Correct intermediate
Curly arrow back from C-H bond to reform

π-ring AND H+ as product
π-ring must be more than 1/2 way down

AND
‘horseshoe’ the right way, i.e. gap towards
C with Cl
ALLOW + sign anywhere inside the

Regeneration of catalyst ‘hexagon’ of intermediate
H+ + AlCl4– → AlCl3 + HCl
Total 16
9 π bonds in benzene are delocalised 1
Total 1

Mark Scheme
10 i 4 ANNOTATE ANSWER WITH TICKS AND

CROSSES ETC
M1
IGNORE p-orbitals overlap to form sigma
p-orbitals overlap (to form pi / π-bonds) ✔ bonds
M2 ALLOW electrons are delocalised in

structure B
π-bond(s) are delocalised in structure B ✔ IGNORE B has delocalised structure or
ring (must be electrons or π-bonds)
M3
ALLOW π-electrons / p-orbital overlap
π-bonds are localised / between two localised / between two carbons in
carbons in structure A structure A
✔ ALLOW p-orbitals overlap with one other
carbon
IGNORE electrons are localised OR
structure A has localised structure (must
be π-bonds / π-electrons / p-orbital overlap)
M4 ALLOW labelled diagram showing overlap
of p-orbitals between two carbon atoms
DO NOT ALLOW C=C in this diagram
Diagram for structure A must show the full

ring for M4 IGNORE C=C in M4 diagram
IGNORE charge density

Diagrams show correct position of
delocalised and localised π-bonds / π-
electrons
DO NOT ALLOW electronegativity
OR correct position of p-orbital overlap ✔
Structures do not need to be labelled A
and B if the description matches the
structure
QWC
Examiner's Comments
requires delocalised / delocalized spelled
correctly and used in correct context
Many excellent answers with clear
diagrams and explanations were seen.
Delocalised electrons in structure B and p-
orbital overlap were the most accessible
marking points.

Mark Scheme
ii structure B / delocalised structure is 2 ALLOW structure B is low in energy

(more) stable ✔ IGNORE structure B is less reactive
ALLOW enthalpy change / hydrogenation

structure B is a better because for benzene is less (negative) than 3 ×
(enthalpy change of hydrogenation for (–)119
benzene is) less (exothermic) than (–) 357 IGNORE more positive than (–)357 kJ
(kJ mol–1) ✔ mol–1
ALLOW enthalpy change is less than 3x
enthalpy change for cyclohexene
ALLOW structure B is more stable by 149
kJ mol–1 (2 marks)
DO NOT ALLOW more / less energy
needed for the reaction
Answer must refer to data given in the
question and must be a comparison
IGNORE 360 kJ mol–1
No marks can be awarded if structure A is
selected
Examiner's Comments
Many used the data given in the question

to compare the enthalpy of hydrogenation
of structure A and structure B but relatively
few candidates scored the other mark for
stating that structure B is better
representation of benzene because it is
more stable. Some candidates confused
cyclohexene with structure A and
incorrectly concluded that the
hydrogenation of benzene is more
exothermic than structure A. Some
incorrectly referred to enthalpy of hydration
or stated that energy is required for the
reaction. Others referred to data they had
memorised rather than using the
information in the question as instructed.
Total 6

Mark Scheme
11 1 ALLOW correct structural OR displayed

OR skeletal formulae OR a combination of
above as long as unambiguous
ALLOW disubstitution at any positions on

✔ benzene ring
Examiner's Comments
Generally well answered. Some candidates

reacted compound B with only one mole of
bromine or three moles of bromine and this
underlines the importance of paying careful
attention to information given in the stem of
the question. Hydrogen, not HBr, was
occasionally formed as the other product.
Total 1

Mark Scheme
12 a Aliphatic = E, H, I, J (1) 3
Alicyclic = E, H, J (1)
Aromatic = F, G (1)
b CnH2n + 1 1 do not allow CnH2n+ 1
c i Equation: 4 ignore state symbols

C6H12O → C6H10 + H2O (1) allow C6H11OH for C6H12O
Calculation: If there is an alternative answer, check

FIRST CHECK THE ANSWER ON THE to see if there is any ECF credit
ANSWER LINE possible using working below
IF answer = 32.7 (%) award 3 marks
% yield must be to 1 dp
theoretical yield = 7.65 / 100 = 0.0765
(mol) (1) allow theoretical and actual yield
calculated in mass
actual yield = 2.05 / 82 = 0.025 (mol) (1)
theoretical yield = 0.0765 × 82 = 6.273 g
% yield = (0.025 / 0.0765) × 100% =
32.7(%) (1) % yield = (2.05 / 6.273) = 32.7(%)
allow ecf from calculated actual and

theoretical yields
ii bromine water is decolourised (1) 2 allow bromine water turns colourless
ignore ‘goes clear’
allow correct structural OR displayed OR

skeletal formula OR mixture of the above
(1)
Total 10

Mark Scheme
13 a i 3 ANNOTATE ANSWER WITH TICKS AND

Dipole shown on C=O bond, Cδ+ and Oδ–, CROSSES
AND curly arrow from the C=O bond to the
Oδ– atom
AND
Curly arrow from π–bond to C in CO2 ✓
________________________________ DO NOT ALLOW the following

intermediate:
Correct intermediate ✓
Curly arrow back from C–H bond to reform

π–ring ✓
π–ring must cover more than 1/2 of the ring

AND
‘horseshoe’ in the correct orientation, ie
gap towards C with COO–
ALLOW + sign anywhere inside the
‘hexagon’ of intermediate
ii 2
Neutralisation ✓ ALLOW acid-base
(In Stage 1) phenol loses H+

AND ALLOW both Stage 1 AND Stage 3 involve
(In Stage 3) carboxylate ion gains H+ ✓ proton transfer

Mark Scheme
iii FIRST CHECK THE ANSWER ON THE 3 ANNOTATE ANSWER WITH TICKS AND
ANSWER LINE CROSSES
IF answer = 7.31 (g) award 3 marks
__________________________________
ALLOW ECF at each stage
ALLOW 3 SF up to calculator value

correctly rounded for intermediate values
actual
100 ALLOW expected mass compound E
n(salicylic acid) produced = =
0.035(0) (mol) ✓ = 4.83 × = 10.733 (g)
theoretical
ALLOW Mass phenol reacted = 0.035 ×
94.0 = 3.29 (g)
n(phenol) = n(salicylic acid) = 0.035(0) ×
= 0.0778 (mol) ✓
ALLOW Mass of phenol used = 3.29 ×

Mass of phenol = 0.0778 × 94.0 = 7.31 (g)
✓
= 7.31 (g)
Note:
1.48 g would get 2 marks
(use of 45.0/100 instead of 100/45.0)
7.30 g would get 2 marks
(use of 0.0777 for moles phenol)

Mark Scheme
b 2
Skeletal formula of aspirin IF skeletal formulae are not used ALLOW

one mark if both the structures of aspirin
AND ethanoic acid are correct
IGNORE names
Skeletal formula of ethanoic acid
Total 10

Mark Scheme
14 a i 1 ALLOW correct structural OR displayed

OR skeletal formulae OR combination of
DO NOT ALLOW —O—Na OR -COO-Na

(covalent bond)
ALLOW —O–
ALLOW delocalised carboxylate
Examiner's Comments
The question asked for the product of the

reaction with excess sodium hydroxide.
Many answers included the product formed
by the reaction of just one of the functional
groups. Most commonly the phenol group
was left unreacted. The mark scheme
permitted the omission of the cation from
the formula of the compound but this
omission was rarely seen.

Mark Scheme
ii (Bromine) would be decolourised / turn 1 IGNORE goes clear

(from orange / red / yellow / brown) to
colourless DO NOT ALLOW other colours for
bromine
OR white precipitate / solid / emulsion
(formed) ✔ IGNORE cream precipitate
DO NOT ALLOW salicylic acid turns

colourless / decolourised
IGNORE temperature / fumes
Examiner's Comments
The observation for the reaction of a

phenol with bromine was very well known
and many candidates offered two correct
observations when only one was required
to score the mark.
iii 1 ALLOW correct structural OR displayed

OR skeletal formulae OR combination of
MUST be all correct to score mark
ALLOW molecular formulae, i.e.

✔ C7H6O3 + Br2 → C7H5O3Br+ HBr
Examiner's Comments
A very well answered question. Most

candidates copied the structural formulae
given in the question. Some made errors
when they unnecessarily converted the
structures into molecular formulae. HBr
was occasionally missing as a product.

Mark Scheme
iv (CH3)2CHOH / CH3CH(OH)CH3 / 1 ALLOW correct structural OR displayed

propan(–)2(–)ol OR skeletal formulae OR combination of
AND acid / H+ / H2SO4 (catalyst) ✔ ALLOW 2-propanol
DO NOT ACCEPT incorrect name or

incorrect formula of alcohol
IGNORE reflux / concentrated (acid)
Examiner's Comments
Many candidates correctly gave the

formula for propan-2-ol and included an
acid catalyst. Common non-scoring
answers omitted the acid or the alcohol or
gave an incorrect name for the alcohol.
b i 4 ALLOW mechanism with Br+ electrophile

(Maximum 3 marks)
No Br2 dipole needed
Curly arrow to Br from ring OR from within IGNORE any equations involving a
the ring halogen carrier
AND curly arrow Br-Br bond to Br ✔
____________________________
____________________________
BUT DO NOT ALLOW intermediate with π-
system covering less than half of ring:
✔ correct intermediate (with charge)

ALLOW + charge anywhere inside the
✔ curly arrow from C—H to reform ring ‘horseshoe’
Horseshoe must have open end towards

Br

Mark Scheme
Apply ecf to error in structure of

intermediate (M2)
+ HBr / H++ Br- ALLOW Kekulé mechanism as shown
✔ Correct products (Maximum 3 marks if Br+ is the

electrophile)
(Br- may be shown in the first step)
ALLOW double bonds in alternate

arrangement
Examiner's Comments
Many fully correct and clearly structured

mechanisms were seen. A proportion of
candidates did not score full marks
because they ignored the information in the
question and based their mechanism on
the Br+ electrophile and did not finish with
HBr as a product. Relatively few
candidates lost marks for incorrectly
positioned curly arrows.

Mark Scheme
ii (In salicylic acid) 3 ALLOW diagram to show movement of

lone pair into ring but delocalised ring must
be mentioned
lone pair / pair of electrons on O(H) / ALLOW lone pair / pair of electrons on
phenol is ∽ (partially) delocalised into the O(H) / phenol is (partially) drawn / attracted
ring ✔ / pulled into delocalised ring
IGNORE ‘activates the ring’

electron density increases / is high ORA ✔
ALLOW more electron rich
DO NOT ALLOW charge density or

electronegativity
Br2 / electrophile is (more) polarised ORA ALLOW (salicylic acid) attracts

✔ electrophiles more/more susceptible to
electrophilic attack
ALLOW Br2 is (more) attracted OR Br2 is

not polarised by benzene
OR induces dipoles (in bromine /
electrophile)
QWC: delocalised / delocalized / Delocalise(d) needed to score the first

delocalise etc. marking point
must be spelled correctly in the correct
context at least once Examiner's Comments
This question was very well answered with

the majority of candidates scoring at least
two marks. The most common errors were
the omitting the words delocalised or lone
pair or failure to use the word delocalised
in the correct context.
Total 11
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Answer all the questions.

1: Benzene is less reactive than cyclohexene

What would the student see during this reaction?

A Bromine water goes from orange to green.

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Which organic products are likely to form?

The results of the tests are shown below.

Test Br2(aq) Na2CO3(aq)

What is the minimum number of C atoms in Y?

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Group Position to which new substituent is

(ii) The reactions of C6H5N(CH3)2 are similar to the reactions of phenol.

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4-Chloromethylbenzene is one of the products of the chlorination of methylbenzene.

Show how AlCl3 behaves as a catalyst.

The carbon–carbon bonds in benzene are all the same length.

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reaction enthalpy change / kJ mol−1

C6H10 + H2→ C6H12 −119

C6H6 + 3H2→ C6H12 −208

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1 mol of compound B reacts with 2 mol of bromine, Br2 by electrophilic substitution.

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Each response may contain more than one letter.

What is the general formula of alkyl groups?

A student carries out this preparation using 7.65 g of compound J.

The student obtains 2.05 g of compound H.

(i) Write an equation for this reaction, using molecular formulae.

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Give your answer to one decimal place.

percentage yield = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ % [4]

Draw the structure of the organic product from the test.

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Calculate the mass of phenol that the chemist uses.

Give your answer to three significant figures.

mass of phenol = _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ _ g [3]

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Draw skeletal formulae for the products of this reaction.

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The flowchart below shows some reactions of salicylic acid.

(ii) Describe what would be observed during reaction 2.

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(iii) Write a chemical equation to represent reaction 2.

(iv) State the reagents and conditions in reaction 3.

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A halogen carrier is not required for this reaction.

The electrophile is Br2.

END OF QUESTION PAPER

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Question Answer/Indicative content Marks Guidance

8 a i 3 IGNORE names throughout

DO NOT ALLOW poly-substituted

DO NOT ALLOW 2-chloro or 4-chloro