2021-23 Curriculum

AS/A2 - Chemistry

16 - Halogenoalkanes
16 – Learning Outcomes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

You should be able to:

 write equations for the reactions of halogenoalkanes when
they undergo:
– nucleophilic substitution, such as hydrolysis, formation of
nitriles, formation of primary amines by reaction with
ammonia
– elimination of hydrogen bromide (for example, from 2-
bromopropane)
 describe and explain the SN1 and SN2 mechanisms of
nucleophilic substitution in halogenoalkanes
 interpret the different reactivities of halogenoalkanes
 explain the uses of fluoroalkanes and fluorohalogenoalkanes
in terms of their relative lack of reactivity
 explain the concern about the effect of chlorofluoroalkanes
on the ozone layer.
1 – Nucleophilic Substitution Reactions
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Introduction
► Halogenoalkanes are used in many industrial chemical
processes.
► Unlike some of the elements from which they are
formed, such as fluorine and chlorine, many
halogenoalkanes are relatively unreactive under
normal conditions.
This leads to their use
as flame retardants
and anaesthetics.
Figure 16.1 An
anaesthetist putting a
patient to sleep before an
operation
1 – Nucleophilic Substitution Reactions
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Introduction
► If you have ever had an operation, you may have a
halogenoalkane to thank for putting you to sleep.
► You might have heard of an early anaesthetic called
chloroform. Its systematic name is trichloromethane.
Nowadays you may receive a gas known as ‘halothane’:

► However, under other conditions, such as high in the

Earth’s stratosphere, some halogenoalkanes react in
completely different ways.
1 – Nucleophilic Substitution Reactions
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Nucleophilic substitution reactions

► We can think of the halogenoalkanes as alkanes that
have one or more hydrogen atoms replaced by
halogen atoms.
Remember that the halogens are the elements in
Group 17 of the Periodic Table, namely fluorine (F),
chlorine (Cl), bromine (Br) and iodine (I).
► The simplest halogenoalkanes, whose molecules
contain just one halogen atom, will have the general
formula CnH2n + 1X, where X is F, Cl, Br or I. The
presence of the halogen atom has a huge effect on
the reactivity of the halogenoalkanes compared with
that of the alkanes.
1 – Nucleophilic Substitution Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

1 Substitution reactions with aqueous alkali, OH–(aq)

► When an aqueous solution of sodium hydroxide is added to
a halogenoalkane, a nucleophilic substitution reaction takes
place.
► The halogen atom in the halogenoalkane is replaced by an
OH, hydroxyl group, so the organic product formed is an
alcohol:

► We can also show this equation as:

CH3CH2Br + OH–  CH3CH2OH + Br–
► The aqueous hydroxide ion behaves as a nucleophile here,
because it is donating a pair of electrons to the carbon atom
bonded to the halogen in the halogenoalkane. This is why
the reaction is called a nucleophilic substitution.
1 – Nucleophilic Substitution Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Hydrolysis of a Halogenoalkane
The reaction is carried out under
reflux in the laboratory. This
enables us to heat the reaction
mixture without evaporating off
the volatile organic compounds in
the reaction flask. The apparatus
is shown in Figure 16.2.
Similar reactions occur with other
halogenoalkanes, but the
reaction rates differ.

Figure 16.2 Reflux apparatus for

hydrolysis of a halogenoalkane.
1 – Nucleophilic Substitution Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Hydrolysis of a Halogenoalkane
We can investigate the rate of hydrolysis using aqueous
silver nitrate solution. The water in the silver nitrate solution
acts as the nucleophile, and again an alcohol is formed. The
reaction is called hydrolysis (meaning ‘breakdown by water’):
CH3CH2Br + H2O  CH3CH2OH + H+ + Br–
It is a very similar reaction to the reaction that takes place
with aqueous alkali.
However, the hydrolysis with water occurs more slowly than
with OH–(aq). This is because the negatively charged
hydroxide ion is a more effective nucleophile than a neutral
water molecule.
From the equation above, you can see that a halide ion, in
this case Br–, is produced in the reaction.
1 – Nucleophilic Substitution Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

1 Substitution reactions with aqueous alkali, OH –(aq)

► On page 175 we used silver nitrate solution to test for
halide ions. Remember that aqueous chlorides give a
white precipitate (silver chloride), bromides give a cream
precipitate (silver bromide) and iodides produce a pale
yellow precipitate (silver iodide).
► The water in the silver nitrate solution will hydrolyse a
halogenoalkane.
► Observing this reaction, we
can time how long it takes
for test tubes containing the
halogenoalkanes and
aqueous silver nitrate
solution to become opaque.
1 – Nucleophilic Substitution Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

1 Substitution reactions with aqueous alkali, OH–(aq)

► We find that:
 the fastest nucleophilic substitution reactions take
place with the iodoalkanes
 the slowest nucleophilic substitution reactions take
place with the fluoroalkanes.
► The substitution reaction involves the breaking of the
carbon halogen bond. Looking at the bond energies

Fluoroalkanes least reactive

Chloroalkanes
Bromoalkanes
Iodoalkanes most reactive
1 – Nucleophilic Substitution Reactions
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1 Substitution reactions with aqueous alkali, OH–(aq)

► (Table 16.1) helps us to explain the rates of reaction.
Notice that the C–I bond is the weakest, so it is broken
most easily. It forms an I– ion during the substitution
reaction.
► This is shown clearly in an ionic equation:

► There is more about the mechanism of nucleophilic

substitution on pages 220–1.
Table 16.1 Bond
energy values of
the carbon–
halogen bonds.
1 – Nucleophilic Substitution Reactions
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2 - Substitution with cyanide ions, CN– (in ethanol)

► In this reaction the nucleophile is the cyanide, CN–, ion.
To carry out the reaction, a solution of potassium
cyanide, KCN, in ethanol (known as an ethanolic or
alcoholic solution of potassium cyanide) is made up.
► This is then heated under reflux with the
halogenoalkane. An ionic equation for this reaction is:

► Note that in the reaction with the cyanide ion, an extra

carbon atom is added to the original halogenoalkane
chain. In this case, bromoethane is converted to
propanenitrile.
1 – Nucleophilic Substitution Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

2 - Substitution with cyanide ions, CN– (in ethanol)

► Sometimes in industry chemists need to make a new
compound with one more carbon atom than the best
available organic raw material (the starting compound).
► Therefore, if we can convert the starting compound to a
halogenoalkane, we can then reflux with ethanolic KCN
to make a nitrile.
► We now have an intermediate
nitrile with the correct number
of carbon atoms.
► We will consider nitriles and
their subsequent conversion to
carboxylic acids and amines
again in Chapter 18, page 231.
1 – Nucleophilic Substitution Reactions
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3 - Substitution with ammonia, NH3 (in ethanol)

► If a halogenoalkane is heated with an excess of
ammonia dissolved in ethanol under pressure, an
amine is formed.

► Here the nucleophile is the ammonia molecule.

Ethylamine is a primary amine, as the nitrogen
atom is attached to only one alkyl group. If the
ammonia is not in excess, we get a mixture of
amine products.
1 – Nucleophilic Substitution Reactions
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3 - Substitution with ammonia, NH3 (in ethanol)

► This is because the primary amine product will act
as a nucleophile itself and will attack
halogenoalkane molecules, forming secondary
amines, and so on.
► The secondary amine formed above would be
(CH3CH2)2NH, called diethylamine. You can read
more about amines in
Chapter 27, page 401.
1 – Nucleophilic Substitution Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Questions
1. a. Why does the hydrolysis of a halogenoalkane
happen more quickly with OH–(aq) ions than with water
molecules?
b. Explain why silver nitrate solution can be used to
investigate the rate of hydrolysis of the
halogenoalkanes. Include ionic equations for the
formation of the precipitates.
2. a. Why can ammonia and amine molecules act as
nucleophiles?
b. When ammonia is reacted with an excess of a
halogenoalkane, a mixture of amines can be formed. If
we start with an excess of 1-bromopropane, give the
structural formula and name of the tertiary amine
formed.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism of nucleophilic substitution in

halogenoalkanes
► Many of the reactions of halogenoalkanes are nucleophilic
substitutions. In these reactions, the nucleophile attacks
the carbon atom bonded to the halogen. Remember from
Chapter 14 that nucleophiles are donors of an electron
pair and are attracted to electron-deficient atoms.
► The carbon–halogen bond is polarised because the
halogen is more electronegative than
carbon. Therefore the carbon atom
carries a partial positive charge as the
electron pair in the carbon–halogen
bond is drawn nearer to the halogen
atom (shown in Figure 16.3).
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism of nucleophilic substitution in

halogenoalkanes
► The halogen atom is replaced by
the nucleophile in the substitution
reaction.

Figure 16.3 The carbon–halogen

bond is polarised.

► There are two possible mechanisms that can operate

in the nucleophilic substitution reactions of
halogenoalkanes.
► The mechanism is determined by the structure of the
halogenoalkane involved in the reaction.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for primary halogenoalkanes (SN2)

► In primary halogenoalkanes containing one
halogen atom, the halogen atom is bonded to a
carbon atom, which is itself bonded to one other
carbon atom and two hydrogen atoms.
► This means that the carbon atom bonded to the
halogen is attached to one alkyl group. For
example, 1-chloropropane,
CH3CH2CH2Cl, is a primary
halogenoalkane.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for primary halogenoalkanes (SN2)

► On page 220 we looked at the hydrolysis of
bromoethane, another primary halogenoalkane.
Figure 16.4 shows the mechanism for that reaction.

Figure 16.4 The mechanism of nucleophilic

substitution in a primary halogenoalkane.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for primary halogenoalkanes (SN2)

► The OH– ion donates a pair of electrons to the δ+ carbon
atom, forming a new covalent bond. At the same time,
the C--Br bond is breaking. The Br atom takes both the
electrons in the bond (an example of heterolytic fission of
a covalent bond, see page 196) and leaves as a Br– ion.
► This mechanism is called an SN2 mechanism. The ‘S’
stands for substitution and the ‘N’ stands for nucleophilic.
The ‘2’ tells us that the rate of the reaction, which I
determined by the slow step in the mechanism (see
page 141), involves two reacting species.
► Experiments show us that the rate depends on both the
concentration of the halogenoalkane and the
concentration of the hydroxide ions present.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for tertiary halogenoalkanes (SN1)

► In a tertiary halogenoalkane, the carbon atom
bonded to the halogen atom is also bonded to
three other carbon atoms
(alkyl groups).
► For example, 2-bromo-2-
methylpropane is a tertiary
halogenoalkane. Its structure
is shown in Figure 16.5.
Figure 16.5 A tertiary
halogenoalkane, 2-bromo-2-
methylpropane.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for tertiary halogenoalkanes (SN1)

► A tertiary halogenoalkane reacts with a hydroxide ion
by a two-step mechanism. The first step in the
mechanism is the breaking of the carbon–halogen
bond.
► This forms a tertiary carbocation, which is attacked
immediately by the hydroxide ion (Figure 16.6).

Figure 16.6 The mechanism of nucleophilic substitution in a

tertiary halogenoalkane.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for tertiary halogenoalkanes (SN1)

► This mechanism is known as an SN1 mechanism.
The ‘1’ tells us that the rate of the reaction only
depends on one reagent, in this case the
concentration of the halogenoalkane, as shown in the
first (slow) step of the mechanism.
► Once again, this breaking of the C--Br bond is an
example of heterolytic fission.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for tertiary halogenoalkanes (SN1)

► The Br– ion forms again, as in the SN2 mechanism, but in
this mechanism a carbocation ion forms.
This does not happen with primary
halogenoalkanes. This is because
tertiary carbocations are more stable
than primary carbocations due to the
inductive effect of the alkyl groups
attached to the carbon atom bonded to
the halogen.
► Alkyl groups tend to release electrons to
atoms attached to them. So a tertiary
carbocation has three alkyl groups donating
electrons towards the positively charged
carbon atom, reducing its charge density.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Mechanism for tertiary halogenoalkanes (SN1)

► This makes it more stable than a primary carbocation, which
just has one alkyl group releasing electrons (Figure 16.7).
► The SN1 mechanism and the SN2 mechanism are both likely
to play a part in the nucleophilic substitution of secondary
halogenoalkanes.

Figure 16.7 The trend in the stability of primary, secondary

and tertiary carbocations.
2 – Mechanism of nucleophilic substitution in halogenoalkanes
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Questions
3. Show the mechanism, including
appropriate curly arrows, for the
hydrolysis of 1-chloropropane,
CH3CH2CH2Cl, by alkali.
4. a. Draw the structure (displayed
formula) of 2-chloro-2-methylbutane.
b. Show the mechanism for the
hydrolysis of 2-chloro-2-
methylbutane by alkali.
3 – Elimination Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Elimination reactions
► Halogenoalkanes also undergo elimination
reactions. An elimination reaction involves the loss
of a small molecule from the original organic
molecule. In the case of halogenoalkanes, this
small molecule is a hydrogen halide, such as HCl or
HBr.
► The reagent used in these elimination reactions is
ethanolic sodium hydroxide:
3 – Elimination Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Elimination reactions
► The original 2-bromopropane molecule has lost an
H atom and a Br atom. We can think of it as HBr
being eliminated from the halogenoalkane. The
ethanolic OH– ion acts as a base, accepting an H+
from the halogenoalkane to form water.
► The C--Br bond breaks
heterolytically, forming a
Br– ion and leaving an
alkene as the
organic product.
3 – Elimination Reactions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Elimination reactions
► Notice the importance of the conditions used in
organic reactions. If we use NaOH(aq), a
nucleophilic substitution reaction
occurs and an alcohol is
produced.
► If we use NaOH(ethanol), an
elimination reaction occurs and
an alkene is produced.

Questions
5. Write a balanced equation for the reaction of
bromoethane with ethanolic sodium hydroxide.
4 – Uses of Halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Uses of halogenoalkanes
► Halogenoalkanes are rarely found naturally but they are
important in the chemical industry. They are frequently
made as intermediates for making other useful substances
but have also found some uses themselves.
► We have already seen at the start of this chapter how some
halogenoalkanes are important anaesthetics, for example
2-bromo-2-chloro-1,1,1-trifluoroethane (halothane).
► One of the essential properties of an anaesthetic is
chemical inertness, and each halothane
molecule contains three very strong
C--F bonds that are difficult to break,
making halothane inert and safe to
use in the aqueous environment
inside the body.
4 – Uses of Halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

Uses of halogenoalkanes
► The non-stick lining of pans is a ‘fluoropolymer’. Its name
is poly(tetrafluoroethene) – often referred to by its trade
name Teflon®. The strength of the C--F bond means that
it can be used at high temperatures during cooking
without breaking down.
► The polymer is now finding uses in ice-skating blades
because of its durability and its ‘low-friction’
properties.
4 – Uses of Halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

CFC substitutes containing fluorine

► CFCs are chlorofluorocarbons. Chemists refer to them as
chlorofluoroalkanes. These organic compounds are all
chemically inert (very unreactive). They are not flammable
and are not toxic.
► These properties made volatile CFCs useful as aerosol
propellants, solvents and as the refrigerants inside
fridges. They were also used as blowing
agents for polymers such as expanded
polystyrene.
► Dichlorodifluoromethane
is an example of a CFC
used for these purposes.
4 – Uses of Halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

CFC substitutes containing fluorine

► When the compounds were discovered in the 1930s,
people could see no drawbacks to using the new ‘wonder
compounds’.
► However, CFCs have caused a serious environmental
issue – the depletion of the ozone layer in the upper
atmosphere.
► The ozone layer protects the Earth by absorbing harmful
UV radiation arriving from the Sun. It
turns out that CFCs are unreactive in
normal conditions, but high up in the
atmosphere they become totally different.
Figure 16.8 Banning the use of CFCs has
meant that the hole in the ozone layer
over Antarctica is now getting smaller.
4 – Uses of Halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

CFC substitutes containing fluorine

► The CFCs can persist in the atmosphere for about a
hundred years. They diffuse up to the stratosphere – and
that’s where the problem starts.
► The UV light from the Sun breaks the C--Cl bonds in the
CFC molecules. This releases highly reactive chlorine
atoms, called chlorine free radicals. These chlorine free
radicals react with ozone molecules.
► In a sequence of chain reactions, it has been estimated
that each chlorine free radical can destroy a million ozone
molecules
(Figure 16.8).
4 – Uses of Halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

CFC substitutes containing fluorine

► Governments have tackled the
problem, and most industrialised
countries have now banned the use
of CFCs.
► Chemists developed new
compounds for fridges and aerosols,
such as hydrofluorocarbons (HFCs):
for example, CH2FCF3. These non-
chlorinated compounds break down
more quickly once released into the
air because of the presence of
hydrogen in their molecules, so they
never rise in the atmosphere as far
as the ozone layer.
4 – Uses of Halogenoalkanes
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

CFC substitutes containing fluorine

► There are now signs that the ozone layer is
recovering from the effects of CFCs. The hole in the
ozone layer is very slowly closing up.
► HFEs are hydrofluoroethers, which are solvents
marketed as ‘low global warming’ and are used in
industry for cleaning and drying. When fluorine
replaces chlorine in a solvent the new compound is
more stable, again due to C--F being stronger than
C--Cl.
Questions
6. How can such unreactive compounds as CFCs
cause so much damage to the ozone layer?
Summary
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

 If one or more of the hydrogen atoms in an alkane

molecule are replaced by halogen atoms, the
compound is called a halogenoalkane.
 Iodoalkanes are the most reactive halogenoalkanes,
whereas fluoroalkanes are the least reactive. This is
explained by the trend in the bond strength of the
carbon–halogen bonds. The C--F bond is the strongest
bond, and the C--I bond is the weakest bond. So the
C--I bond is most easily broken during its reactions.
 Halogenoalkanes are attacked by nucleophiles. This
happens because the carbon bonded to the halogen
carries a partial positive charge due to the higher
electronegativity of the halogen. Halogenoalkanes
undergo nucleophilic substitution.
Summary
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

 Suitable nucleophiles include aqueous alkali, OH–

(aq), cyanide, CN–, and ammonia, NH3.
 The reaction with OH– ions (or with water) is known
as hydrolysis, and an alcohol is formed.
 Halogenoalkanes will also undergo elimination
reactions when heated with ethanolic sodium
hydroxide, forming alkenes.
 The fluoroalkanes and fluorohalogenoalkanes have
many uses, including anaesthetics, solvents,
refrigerants and aerosol propellants.
 Chlorofluoroalkanes have been responsible for
damaging the Earth’s ozone layer, but alternative
inert compounds, such as fluoroalkanes, are now
replacing the use of CFCs.
16 – End of Chapter Questions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

1. 1-bromobutane will undergo

reactions when heated, as shown
by reactions A and B.
a. For reactions A and B give the
reagents used in each case.
[2]
b. Reaction A was repeated using 1-iodobutane instead of 1-
bromobutane. Explain any difference in the rate of reaction observed.
[2]
c. What type of organic reaction is A?
[1]

?
d. Show the mechanism for reaction A.
[3]
e. Reaction A was repeated with 2-bromo-2-methylpropane instead of 1-
bromobutane.
i. Name the organic compound formed.
[1]
ii. The mechanism of the reaction with 2-bromo-2-methylpropane
differs from the mechanism of reaction A. Describe how the
mechanisms differ.
16 – End of Chapter Questions
1 - Nucleophilic Substitution Reactions 2 - Mechanisms 3 – Elimination Reactions 4 - Uses 5 - Questions

2. Bromochlorodifluoromethane has been used in

fire extinguishers. However, its breakdown
products were found to be toxic.
a. Draw the displayed formula of
bromochlorodifluoromethane.
[1]
b. CF3CH2F is being introduced as a
replacement for various CFCs in
?
refrigerants and aerosols. Name this
compound.
[1]
c. What is the main environmental problem