Lesson Plan

Lesson : Reactions of Toluene

Aim :

To study the chemical reactions of toluene.

Learning Outcomes :

By the end of the lesson, students will be able to:

• state and explain electrophilic substitution reactions for toluene.

• explain the oxidation of the side-chain of toluene.

• determine the products of halogenation of toluene in the presence of light.

Assumed prior knowledge :

Students should already be familiar with:

1. the electrophilic substitution reactions of benzene.

2. the effects of subtituents on the reactivity and orientation in electrophilic aromatic

substitution reactions.

Underlying Principles

1. Making the invisible, visible.

2. Enabling students to know what to look for.

Differentiation

Questions in the student notes are designed to enable all students to complete the activity.
The pop-up answers are provided for the students to view when they have considered their
responses. Worksheet questions include questions that require recall, understanding and
application of the new concepts learned.

© 2004 Ministry of Education Malaysia. All Rights Reserved. Page 1 of 1

Development of Lesson :

No. Steps Strategy Resources

1 Set Induction.
(Ascertaining prior • Teacher to get students to recall the
knowledge and electrophilic aromatic substitution
introducing lesson reactions of benzene that they have
topic for the day). learned in the previous lesson. Teacher
to get students to recall the effect of
substituents in monosubstituted benzene
derivatives on the reactivity and
orientation in such reactions.
• Teacher to get students to predict the
reactivity of toluene towards electrophilic
aromatic substitution.

2 Student Activity Teacher to go through Activity 1 with the • Courseware

students.

Activity 1 : Electrophilic substitution

reactions

Students get to compare the electrophilic

aromatic substitution reactions of toluene
with those of benzene. They get to learn
that the presence of the methyl
substituent in toluene enables the
compound to react more readily than
benzene and results in a mixture of
ortho and para disubstituted compounds.

Teacher to get students to recall the types

of reactions that alkanes can undergo.
Teacher to point out similarity between the
methyl side chain of toluene and an
alkane towards free radical substitution.
Teacher to go through Activity 2 with the
students.

Activity 2 : Side-chain reactions

Students get to view the two types of side-

chain reactions of toluene i.e. free radical
substitution and oxidation of the side
chain.

3 Evaluation • Students to answer questions in the • Worksheet

student worksheet on their own.

4 Extension activity • Students to read up reference materials • References

on their own.

© 2004 Ministry of Education Malaysia. All Rights Reserved. Page 2 of 2

Worksheet Answers

1. Electrophilic substitution reactions

1.1 a. i. CH3 CH3

Br

Br

ii. CH3 CH3

SO3H

SO3H

b. The methyl group in toluene releases electrons and activates the

benzene ring towards electrophilic substitution. Hence, toluene undergoes
electrophilic substitution much more readily than benzene.

1.2 a. Concentrated nitric acid and concentrated sulphuric acid.

b. i. An electrophile is an electron-deficient species which can accept a

pair of electrons.

ii. NO2+

iii. HNO3 + 2H2SO4 NO2+ + H3O+ + 2HSO4-

or
HNO3 + H2SO4 NO2+ + HSO4- + H2O

1.3 a. Friedel-Crafts reaction / Electrophilic substitution reaction

b. CH3 CH3
CH3

CH3

© 2004 Ministry of Education Malaysia. All Rights Reserved. Page 3 of 3

2. Side-chain Reactions

2.1 a. P : (Chloromethyl)benzene
Q : 2-Chloromethylbenzene or o-chloromethylbenzene

b. i. Free radical substitution

ii. Presence of sunlight/uv light
iii. C6H5CHCl2 , C6H5CCl3

c. i. Electrophilic substitution
ii. Presence of AlCl3 catalyst
iii.
CH3

Cl

2.2 a. Benzoic acid

b. Oxidation

c. CH3 COOH

+ 3[O] + H2O

d. CH2CH3 COOH

+ 6[O] + CO2 + 2H2O

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