Question and Answer Chapter 7: Arenes

1. (a) State the general formula for arenes.

CnH2n-6y, where y is the number of cyclic rings in the arene.

(b) Describe aromaticity, Kekule structure and resonance structure for

benzene.

Aromaticity
The property of conjugated cycloalkenes associated with the extra stability of
electrons in π systems that can be delocalise in aromatic compound. There are
four properties of aromatic compounds:
a) It must be cyclic
b) It must be conjugated (i.e. all atoms around the ring must be able to
participate in π-bonding through resonance)
c) It must be flat (planar) molecule
d) Obeys Huckel’s rule which contains (4n+2) π electrons, where
n= 0, 1, 2, 3, …
Kekule structure

The carbons are arranged in a hexagon, and he suggested alternating

double and single bonds between them. Each carbon atom has hydrogen
attached to it.

or

Kekule structure of benzene

Resonance structure

The circle represents the delocalised electrons, and each corner of the
hexagon has a carbon atom with hydrogen attached.

delocalise
=

Resonance structure of benzene

Each carbon atom in benzene is joined to two other similar carbon uses the
sp2 hybrids to form sigma bonds with two other carbons and one hydrogen
atom
2. Why benzene is more stable than aliphatic alkenes?

The presence of the delocalised electrons makes benzene stable

3. Give the IUPAC name of the following compound.

(a) (b) (c)

F H3C O F

1,2-difluorobenzene/
fluorobenzene o-difluorobenzene
acetophenone

(d) (e) (f)

Cl COOH Br
CH3 Cl NO 2

1-chloro-2-fluorobenzene
2-methylbenzoic acid 2-bromo-1-chloro-3-
nitrobenze

(g) (h)

OH
CH 2CH 3 CH3

CH3

CH3 3-benzylheptane

2-ethyl-4-methylphenol

4. Draw a complete structural formula for each of the following compounds:

(a) ethylbenzene

CH3
C
H2
(b) benzaldehyde

O
C

(c) p-dibromobenzene
Br

Br
(d) 3-nitroaniline
 O

N+ NH2
-
O

(e) 2-chloro-3-fluorotoluene

CH3

Cl

F
(f) 3-phenylheptane

H2
H3C C CH CH3
C C C
H2 H2 H2

5. Shows three structural isomers for dimethylbenzene (C8H10).

CH3
CH3

CH3
CH3

o-dimethylbenzene m-dimethylbenzene p-dimethylbenzene

6. Benzene is insoluble in polar solvent. Give the other three physical properties for
benzene.

a) Colourless liquid at room temperature

b) A characteristics smell
c) Insoluble in polar solvents
d) Melting point of benzene is 6oC
e) Boiling point of benzene is 80oC
f) Toxic

7.
 A
D

B r2, F e B r3
C l2 , u v O

+ C
KM nO 4 / H C H 3C l HNO H3C Cl
3
E C B H
 A lC l3 H 2S O 4,  A lC l3
C l2 F e C l3

F + G

(a) Based on the reaction scheme above, draw the structural formula for
compound A to H.
A: B: C: D:

Br NO 2 CH3 CH 2Cl

E: F: G: H:

CH3

COOH CH3 NO 2

Cl
CH3

Cl O

(b) Show the mechanism for the formation of compound C.

STEP 1: Formation of ekectrophile
AlCl3 + CH3Cl → CH3+ + AlCl4-

STEP 2: Formation of Arenium ion

H CH3 H CH3 H CH3

H + +
CH3+
+
+
resonance-stabilized carbocation
STEP 3: Deprotonation
 H CH3 CH3

(c) Explain why activating group, such as –OH is ortho and para director. Give
example of compound from the reaction scheme.
D= -OH group
The lone pair electrons on D atom (the electron-donating group) can shift to form a
carbon-D double bond, causing the migration of the  electrons in one of the
carbon-carbon double bonds giving rise to the resonance structures

+ D + D +D + D
D

Groups direct as electrophile to the ortho-para positions

The delocalisation causes an increase in the electron density on C-2, C-4 and C-6.
As a result, they are more susceptible to attack by electrophiles than C-3 and C-5.
Example: Compound F and G

(d) Explain why deactivating group, such as –NO 2 is meta director. Give
example of compound from the reaction scheme.

W= -NO2 group

The electron withdrawing effect (W) causes the benzene ring to acquire positive
charge that is delocalized over C-2, C-4 and C-6 as shown in Figure 7.6.

W -W -W -W -W

+ +
+ +

+
+

Groups direct as electrophile to the meta positions

As a result the electron density at C-3 and C-5 is higher than those on C-2, C-4
and C-6. This makes C-3 and C-5 more susceptible to attack by electrophiles.

Example: compound H

8. Compound P (C2H4) which is an alkene undergo reaction with HCl to produce

compound Q (C2H5Cl). Reaction of compound Q with benzene in the presence of
AlCl3 as catalyst produce compound R. Then, nitration of compound R in the
presence of H2SO4 produce two compounds, S and T. But, when compound R is
reacted with hot acidified solution of alkaline KMnO 4 gives compound U.

Deduce the structure of compounds P to U.

P: Q:

H2C CH2 H3C CH2Cl

R: S: T: U:

CH3 CH3 CH3

H2C H2C H2C COOH

NO 2

NO 2