Centre for Higher Secondary Education Department of Chemistry

REVISION WORKSHEET ON ARENES

1 The delocalised electrons in benzene result from the overlap of

A s orbitals to form σ bonds
B s orbitals to form π bonds
C p orbitals to form σ bonds
D p orbitals to form π bonds
2 The reaction of ethene with bromine occurs under normal laboratory conditions but
the reaction of benzene with bromine to form bromobenzene requires heat and the
presence of a catalyst.
The best explanation for the difference in reactivity is that the delocalised electrons in
benzene
A repel electrophiles
B result in a kinetic barrier to intermediate formation
C result in benzene having an endothermic enthalpy of formation
D make benzene thermodynamically stable with respect to the formation of
bromobenzene
3 The enthalpy change of hydrogenation of cyclohexene is −120 kJ mol−1.

What is the approximate enthalpy change of hydrogenation of benzene, in kJ mol−1?

A −150
B −210
C −360
D −510
4 Which reagent and catalyst will convert benzene into phenylethanone?

Reagent Catalyst
A Ethanal Aluminium chloride
B Ethanal Platinum
C Ethanoyl chloride Aluminium chloride
D Ethanoyl chloride Platinum

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Centre for Higher Secondary Education Department of Chemistry

5 Chlorine reacts with methylbenzene in the presence of ultraviolet light.

Which of these is a product of this reaction? A

6 This question is about aromatic amines and amino acids.

(a) A synthesis of phenylamine is shown.

Benzene is converted into nitrobenzene in Step 1 using a mixture of concentrated nitric

acid and concentrated sulfuric acid. The electrophile is NO2 + .
A student drew a mechanism for the reaction.

Describe the three changes needed to correct this student’s mechanism. (3)
• the curly arrow should go (from the benzene ring/ π bond / delocalised electrons / inside
the hexagon and) towards the nitrogen / NO2+ (1)
• the open end of the ‘horseshoe’ should be pointing towards the tetrahedral carbon /
carbon with 4 bonds (1)
• the curly arrow should start from the (C-H) bond (1)

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Centre for Higher Secondary Education Department of Chemistry

7 This question is about benzene and some of its compounds.

*(a) In 1865, Kekulé suggested that the benzene molecule was a six-membered carbon
ring with alternate double and single bonds.

However, this suggestion did not fully explain the structure and stability of benzene.
State and explain three different types of evidence that led to this structure of
benzene being rejected, in favour of benzene with a ring of delocalised electrons. (3)

ALLOW reverse arguments for Kekule structure Any three points from
Type of reaction
Benzene reacts by (mostly electrophilic)substitution OR does not react by
(electrophilic) addition OR
Benzene does not react like alkenes /does not decolourise bromine water
ALLOW
Other suitable reactions /benzene needs a catalyst /halogen carrier to react with bromine (1)
Di-substitution
There are only 3 isomers of di-substituted compounds (not 4) OR
Some di-substituted compounds are the same, e.g. 1,2 and 1,6 (1)
Thermochemical
Benzene’s (standard) enthalpy (change) of hydrogenation is less exothermic than if it had
(three localised C=C) double bonds / is not three times the value for three (localised C=C)
double bonds
ALLOW
Benzene is more stable by ~150 kJ mol-1
OR
stated enthalpies (of hydrogenation) −205 to −210 kJ mol-1 for benzene and −360 kJ mol-1
for 3 (localised C=C) double bonds
OR
(Standard) enthalpy (change) of combustion is less exothermic than if it had three (localised
C=C) double bonds (1)
X-ray diffraction – does not need to be
mentioned
The C-C bond lengths in benzene are midway between that of a single bond and a double
bond / are all the same length
OR
Benzene is a regular hexagon (and Kekule structure is not) (1)

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Centre for Higher Secondary Education Department of Chemistry

Infrared
The infrared spectrum for benzene has a peak for an aromatic C=C at a different
wavenumber / absorption / frequency to an alkene C=C OR
Benzene has peaks at 1600, 1580, 1500,1450 (cm−1) rather than 1669 – 1645 (cm−1) (1)
Electron density map
Benzene shows an even spread of electrons (1)
(b) Benzene reacts with a mixture of concentrated nitric acid and concentrated sulfuric acid
to form nitrobenzene.
(i) Give the mechanism for this reaction, including an equation for the formation of the
electrophile. (4)
H2SO4 + HNO3 → NO2+ + H2O + HSO4−
OR
H2SO4 + HNO3 → H2NO3+ + HSO4−
and
H2NO3+ → NO2+ + H2O
OR
2H2SO4 + HNO3 → NO2 + + H3O+ + 2HSO4−
IGNORE state symbols, even if incorrect (1)

(ii) The preparation of nitrobenzene is usually carried out between 50°C and 60°C.
Explain why the temperature used should not be higher or lower. (2)
Higher temperature causes multiple substitution of NO2 groups / formation of
dinitrobenzene / formation of trinitrobenzene
ALLOW further nitration / substitution (1)
At lower temperature reaction is (too) slow (1)
(c) Benzene reacts with pure bromine when heated under reflux in the presence of a Friedel-
Crafts catalyst. Phenol reacts with bromine water at room temperature.
(i) Write the equation for the reaction between phenol and excess bromine water. (2)

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Centre for Higher Secondary Education Department of Chemistry

Formula of organic product (1)

Rest of equation correct (1)

*(ii) Explain why phenol reacts with bromine under much milder conditions than those
required for the reaction between benzene and bromine. (2)
MP1
Lone pair of electrons on oxygen (may be shown on a diagram)
and
EITHER
Overlaps with pi cloud /delocalized electrons / delocalised system
OR
Feeds into / donates into / interacts with (benzene) ring /delocalized electrons / delocalised
system
OR
Increases the electron density of the (benzene) ring (1)
MP2
(Increased electron density) makes the ring more susceptible to electrophilic attack
ALLOW phenol is a better nucleophile (1)
(d) 1-chloro-1-phenylethane is found in some fruits, such as apples, and is used to make
fragrances. It can be synthesised from benzene in three steps.

(i) Identify, by name or formula, the reagent and catalyst used in Step 1. (2)
Ethanoyl chloride / CH3COCl (1)
aluminium chloride / AlCl3 / iron(III) chloride / FeCl3 (1)

(ii) Draw the structure for Compound X. (1)

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Centre for Higher Secondary Education Department of Chemistry

(iii) Identify, by name or formula, the reagent used in Step 2. (1)

Lithium aluminium hydride / LiAlH4 / lithium tetrahydridoaluminate((III)) /
sodium borohydride / sodium tetrahydridoborate / NaBH4
(iv) Identify, by name or formula, the reagent used in Step 3. (1)
Phosphorus(V) chloride / phosphorus
pentachloride / PCl5

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