Lesson Plan

Lesson : Haloalkanes (II)

Aim :

To study the relative reactivity of haloalkanes and the effect of some haloalkanes on the
environment.

Learning Outcomes :

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

• explain the relative reactivity of primary, secondary and tertiary haloalkanes

according to the types of mechanism; SN1 and SN2

• explain the relative rate of hydrolysis of chloroalkanes, bromoalkanes and

iodoalkanes

• explain the difference in reactivity of chlorobenzene and chloroalkanes in hydrolysis

reactions

• explain the effect of some haloalkanes on the environment.

Assumed prior knowledge :

Students should already be familiar with :

1. the nomenclature and classification of haloalkanes

2. the concept of nucleophilic substitution reactions in haloalkanes.

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 3

Development of Lesson :

No. Steps Strategy Resources

1 Set Induction.
(Ascertaining prior • Teacher to get students to recall the
knowledge and IUPAC names of haloalkanes and how
introducing lesson they are classified as primary, secondary
topic for the day). and tertiary. Teacher to go through the
general mechanism of nucleophilic
substitution reactions of haloalkanes.
• Teacher to point out lesson objectives for
the day.

2 Student Activity Teacher to go through Activities 1 and 2 • Courseware

with the students.

Activity 1 : Nucleophilic substitution

mechanisms

Students are first introduced to the fact

that there are two types of mechanism
involved in nucleophilic substitution
reactions of haloalkanes. They are then
shown the steps involved in both SN1 and
SN2 mechanisms.

Students are also shown an experiment

to compare the rate of precipitate
formation by a chloroalkane, a
bromoalkane and an iodoalkane with
silver nitrate solution. Finally, they are
shown that chlorobenzene is less reactive
than chloroalkanes due to delocalisation
of the p electrons of the chlorine atom into
the benzene ring.

Activity 2 : Effect on the environment

Students are shown how

chlorofluorocarbons (CFCs) destroy the
ozone layer in the stratosphere and how
the use of DDT can result in its
accumulation in the human body causing
harm to the nervous system.

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 3

Worksheet Answers

1. Nucleophilic substitution mechanisms

1.1 a. SN1 for tertiary haloalkane

SN2 for primary haloalkane

b.
i. CH2CH2CH3 CH2CH2CH3 _ CH2CH2CH3
slow  fast
NC− + H  C  Br NC….….C…….Br NC  C  H + Br−

H H H H

ii. CH3 CH3

 slow 
CH3CH2  C  Br CH3CH2  C+ + Br−
 
CH3 CH3

CH3 CH3
 fast 
CH3CH2  C+ + CN− CH3CH2  C  CN
 
CH3 CH3

1.2 a. CI CH3
 
CH3CH2CH2CI > CH3CH2CHCH3 > CH3  C  CI

CH3
b. CH3 CH3 CH3
  
CH3  C  Br > CH3  CH  CH  CH3 > CH3  CH  CH2  Br
 
CH3 Br

1.3 a. Alcoholic silver nitrate solution

b. Yellow, silver iodide
c. 2-Iodo-2-methylbutane
d. 2-Iodo-2-methylbutane > 2-Iodopentane > 1-Iodopentane

2. Effect on the environment

2.1 a. Chlorofluorocarbon
b. CF3Cl / CF2CI2 / CFCI3
c. Inert and non-toxic
Aerosol propellants and refrigerants
d. CFCs cause ozone depletion / destroys the stratosphere ozone layer which
filters out most of the sun’s harmful uv radiation.
e. HFC (Hydrofluorocarbon) does not contain any Cl atom. Thus, it does not
release damaging chlorine radicals that destroy the ozone layer.

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