Lesson Plan

Lesson : Arenes (III)

Aim :

To study the effect of substituents on electrophilic substitution reactions of benzene.

Learning Outcomes :

By the end of the lesson, students will be able to identify the effects of some substituents on
the reactivity and orientation in electrophilic aromatic substitution reactions.

Assumed prior knowledge :

Students should already be familiar with :

1. the structure and bonding of benzene and its derivatives.

2. the nomenclature of benzene derivatives.

3. the general mechanism of 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 substitution reactions of
introducing lesson benzene.Teacher to get students to draw
topic for the day). all the possible structural isomers of
disubstituted benzene derivatives.
• Teacher to point out that the ease of
electrophilic substitution of a second
hydrogen atom at the benzene ring and
the position of the second substituent, is
dependent on the first substituent.

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

the students.

Activity 1 : Effect of substituents

Students get to learn that certain

substituents activate/deactivate the
benzene ring towards electrophilic
substitution reactions at the benzene ring.
They also get to learn that activating
substituents will bring about
electrophilic substitution at the positions
ortho and para to themselves while
deactivating groups except halogens are
meta directors.

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. Effect of substituents

1.1 B

1.2 1,3-dinitrobenzene < benzene < phenol

1.3 a. The –NH2 substituent in aniline makes the benzene ring more reactive by
releasing electrons to stabilize the arenium ion that is formed during the
reaction. Hence, the reaction can take place at a lower temperature.

b. NH2 NH2
Br

Br

1.4 a. Br Br Br
Br

Br
Br
1,2-Dibromobenzene 1,3-Dibromobenzene 1,4-Dibromobenzene

b. The major products are 1,2-dibromobenzene and

1,4-dibromobenzene. This is because bromine is an ortho-para
directing substituent.

c. Br Br Br
Br Br Br

Br
Br

Br Br
Br

Br Br

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

1.5 a. CH3 CH3
Cl

Cl

b. COCH3

Cl

c. COOH

Cl

1.6 NO2

O2N NO2

© 2004 Ministry of Education Malaysia. All Rights Reserved. Page 4 of 4