MBC 233.

1 [Organic Chemistry]

Alkyl Halides
Dr. Hamilton Opurum
1
Background
• Alkyl halides, (haloalkanes), are
compounds where one or more hydrogen
atoms in an alkane have been replaced by
halogen atoms such as fluorine, chlorine,
bromine, or iodine.
• They are important in organic chemistry
due to their diverse applications in
synthesis and industry.

2
Learning Guide
• Introduction to Alkyl Halides • Stereochemistry
• Nomenclature • Uses and Applications
• Physical Properties • Interactive Activities
• Preparation Methods • Collaborative Learning
• Reactivity • Assessment

3
Introduction to Alkyl Halides:
An alkyl halide is another name for a
halogen‐substituted alkane.
The carbon atom, which is bonded to
3
the halogen atom, has sp hybridized
bonding orbitals and exhibits a
tetrahedral shape.
4
Alkyl halide
Due to electronegativity differences
between the carbon and halogen
atoms, the σ covalent bond between
these atoms is polarized, with the
carbon atom becoming slightly
positive and the halogen atom
partially negative.
5
Alkyl halide
Halogen atoms increase in size and
decrease in electronegativity going
down the family in the periodic table.
Therefore, the bond length between
carbon and halogen becomes longer
and less polar as the halogen atom
changes from fluorine to iodine.
6
Nomenclature:
• Alkyl halides, also known as haloalkanes or alkyl halogen
compounds, are organic compounds containing one or more
halogen atoms (fluorine, chlorine, bromine, or iodine)
bonded to an alkyl group.
• The general formula for alkyl halides is R-X, where R
represents an alkyl group (a chain of carbon atoms) and X
represents a halogen atom.

7
Common examples of alkyl halides
• Chloromethane (methyl chloride, CH3Cl)
• Bromoethane (ethyl bromide, CH3CH2Br)
• Chloroform (trichloromethane, CHCl3)
• Bromopropane (propyl bromide,
CH3CH2CH2Br)
• Iodoethane (ethyl iodide, CH3CH2I)
8
Classification of Alkyl Halides
• Alkyl halides are classified based on the number of halogen
atoms attached to the alkyl group
• Primary (1°) Alkyl Halides: The halogen atom is bonded to a
carbon atom that is attached to only one other carbon atom.
• Secondary (2°) Alkyl Halides: The halogen atom is bonded
to a carbon atom that is attached to two other carbon atoms.
• Tertiary (3°) Alkyl Halides: The halogen atom is bonded to a
carbon atom that is attached to three other carbon atoms.

9
Importance
• Alkyl halides are important in organic synthesis and are
used as intermediates in the production of various organic
compounds.
• They undergo various chemical reactions, including
nucleophilic substitution, elimination, and reactions with
metals, to form new compounds.
• Alkyl halides are also used as solvents, refrigerants, and in
the production of pharmaceuticals, agrochemicals, and
plastics.
10
Physical properties
 Alkyl halides have little solubility in water but
good solubility with nonpolar solvents, such
as hexane.
 Many of the low molecular weight alkyl
halides are used as solvents in reactions that
involve nonpolar reactants, such as bromine.

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The boiling points of different alkyl halides
containing the same halogen increase with
increasing chain length.
For a given chain length, the boiling point
increases as the halogen is changed from
fluorine to iodine.
For isomers of the same compound, the
compound with the more highly‐branched alkyl
group normally has the lowest boiling point.
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 Table summarizes data for some representative
alkyl halides.

13
 Alkyl halides are named using the IUPAC rules
for alkanes.
 Naming the alkyl group attached to the halogen
and adding the inorganic halide name for the
halogen atom creates common names.

14
Preparation Methods:
• Various methods for synthesizing alkyl
halides, include:
–Halogenation of alkanes.
–Halogenation of alkenes.
–Nucleophilic substitution of alcohols.
–Radical halogenation
15
Alkyl halide formation
 Alcohols are converted to alkyl halides by S N1 and S N2
reactions with halogen acids.

Primary alcohols favor S N2 substitutions while S N1 substitutions occur

mainly with tertiary alcohols.
16
 A more efficient method of preparing alkyl halides from
alcohols involves reactions with thionyl chloride (SOCl 2).

 This reaction is rapid and produces few side reaction

products.
 In addition, the sulfur dioxide and hydrogen chloride formed
as byproducts are gasses and therefore easily removed from
the reaction.
 Mechanistically, the alcohol initially reacts to form an
inorganic ester.
17
The chloride ion produced by this reaction, acting as a nucleophile, attacks the
ester in an S N2 fashion to yield molecules of sulfur dioxide, hydrogen chloride,
and an alkyl halide.

Because the reaction proceeds mainly by an S N2 mechanism, the alkyl halide

produced from an optically active alcohol will have the opposite relative
configuration from the alcohol from which it was formed.

18
Because thionyl bromide is relatively unstable, alkyl bromides are
normally prepared by reacting the alcohol with phosphorous tribromide
(PBr 3).

19
This reaction proceeds via a two‐step mechanism. In the first step, the alcohol reacts
with the phosphorous tribromide.

The second step is an S N1 or S N2 substitution in which the bromide ion displaces the
dibromophosphorous group.

In a similar manner, alkyl iodides are prepared by reacting an alcohol

with phosphorous triiodide.
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Preparation of Alkyl Halides
Two methods are commonly used to
prepare alkyl halides.

Hydrogen halide addition to an alkene

Reaction of alcohols with sulfur and
phosphorous halides

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Hydrogen halide addition to an alkene
 Halogen halides add across carbon‐carbon double bonds.
 These additions follow Markovnikov's rule,
 The positive part of a reagent (a hydrogen atom, for
example) adds to the carbon of the double bond that
already has more hydrogen atoms attached to it.
 The negative part adds to the other carbon of the
double bond.
 Such an arrangement leads to the formation of the more
stable carbocation over other less‐stable intermediates.

22
Hydrogen halide addition to an alkene

23
Reaction of alcohols with sulfur and phosphorous
halides
 Alcohols can be converted to alkyl halides by reaction
with thionyl chloride, SOCl 2·, phosphorous trichloride,
PCl 3·, phosphorous pentachloride, PCl 5·, or
phosphorous tribromide, PBr 3.
 For example, ethyl chloride or ethyl bromide can be
prepared from ethyl alcohol via reactions with sulfur and
phosphorous halides.

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Reaction of alcohols with sulfur and
phosphorous halides

25
REACTIONS OF ALKYL HALIDES

 Nucleophilic substitution reaction

 Elimination reactions

 Grignard reaction

26
Nucleus and Nucleophiles
 A nucleus is any atom that has a partial or fully positive charge associated
with it.
 A nucleophile is an atom or group that is attracted to a source of partial
or full positive charge.
 Alkyl halides act as a nucleus because of the great electronegativity
differences between the carbon atom and the halogen atom directly
bonded to it.
 This great electronegativity difference causes the electron density in the
overlap region between the carbon and halogen atoms to be pulled
toward the halogen atom.
 This shifting of electron density in the molecule makes the carbon atom
partially positive (the nucleus) and the halide ion partially negative (the
incipient leaving group).
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This Figure illustrates the effect of
electronegativity differences on bond polarity.

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 Electrons in the overlap region between the carbon
and the halogen atoms are attracted to the more
electronegative halogen atom.
 The carbon atom, which now has less of a share of
the bonding electrons, becomes partially positive,
and the halogen atom, which has a greater share of
these electrons, becomes partially negative.
 Remember that a nucleophile is a substance that has
a pair of electrons that it can donate to another atom.

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 The weaker the forces of attraction holding the
electron pair to the original molecule, the more
readily this molecule will share the electrons and
the stronger the resulting nucleophile will be.
 The weakest held electrons on an atom are the
non-bonding electron pairs.
 Electrons in π bonds, although held more strongly
than nonbonding electrons, are also loosely held
and easily shared, making unsaturated
compounds relatively good nucleophiles.
 Because they possess a negative charge, anions
are always better nucleophiles than their
conjugate acids.
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Nucleophilic Substitution Reactions
 Alkyl halides undergo many reactions in which a
nucleophile displaces the halogen atom bonded to the
central carbon of the molecule.
 The displaced halogen atom becomes a halide ion.

31
Some typical nucleophiles are:
the hydroxy group ( −OH)
−
the alkoxy group (RO )
and the cyanide ion C N

32
Reaction of these nucleophiles with an alkyl halide (R & bond; X) gives
the following reactions and products:

The halogen ion that is displaced from the carbon atom is

called the leaving group, and the overall reaction is called
a nucleophilic substitution reaction.
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Leaving Group
 For a molecule to act as a nucleus or substrate in a
nucleophilic substitution reaction, it must have both a
polar bond and a good leaving group.
 For an atom or a group to be a good leaving group, it
must be able to exist independently as a relatively stable,
weakly basic ion or molecule.
 Groups that act as leaving groups are always capable of
accommodating the negative charge through a high
electronegativity or by delocalization.
 Because halogen atoms have high electro-negativities
and form relatively stable ions, they act as good leaving
groups.
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Nucleophilic Substitution Reactions:Mechanisms
 Experimental data from nucleophilic substitution reactions on
substrates that have optical activity (the ability to rotate
plane‐polarized light) shows that two general mechanisms exist for
these types of reactions.
 The first type is called an S N2 mechanism.
 This mechanism follows second‐order kinetics (the reaction rate
depends on the concentrations of two reactants), and its
intermediate contains both the substrate and the nucleophile and
is therefore bimolecular.
 The terminology S N2 stands for ―substitution nucleophilic
bimolecular.‖

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S N1 mechanism
• The second type of mechanism is an S N1 mechanism.
• This mechanism follows first‐order kinetics (the
reaction rate depends on the concentration of one
reactant), and its intermediate contains only the substrate
molecule and is therefore unimolecular.
• The terminology S N1 stands for ―substitution
nucleophilic unimolecular.‖

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SN2 mechanism
 The alkyl halide substrate contains a polarized carbon
halogen bond.
 The SN2 mechanism begins when an electron pair of the
nucleophile attacks the back lobe of the leaving group.
 Carbon in the resulting complex is trigonal bi-pyramidal in
shape.
 With the loss of the leaving group, the carbon atom again
assumes a pyramidal shape; however, its configuration is
inverted.

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The S N2 mechanism can be illustrated as shown in Figures 1 & 2.

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 Notice that in either picture, the intermediate shows both the nucleophile and
the substrate.
 Also notice that the nucleophile must always attack from the side opposite
the side that contains the leaving group.
 This occurs because the nucleophilic attack is always on the back lobe
(antibonding orbital) of the carbon atom acting as the nucleus.
 S N2 mechanisms always proceed via rearward attack of the nucleophile on
the substrate.
 This process results in the inversion of the relative configuration, going from
starting material to product.
 This inversion is often called the Walden inversion, and this mechanism is
sometimes illustrated as shown below

39
Steric hindrance
 S N2 reactions require a rearward attack on the carbon bonded to
the leaving group.
 If a large number of groups are bonded to the same carbon that
bears the leaving group, the nucleophile's attack should be
hindered and the rate of the reaction slowed.
 This phenomenon is called steric hindrance.
 The larger and bulkier the group(s), the greater the steric
hindrance and the slower the rate of reaction.
 Table 1 shows the effect of steric hindrance on the rate of
reaction for a specific, unspecified nucleophile and leaving group.
 Different nucleophiles and leaving groups would result in different
numbers but similar patterns of results.

40
S N2 reactions give good yields on 1° (primary) alkyl halides, moderate yields on
2° (secondary) alkyl halides, and poor to no yields on 3° (tertiary) alkyl halides.

41
Solvent effects
 For protic solvents (solvents capable of forming
hydrogen bonds in solution), an increase in the
solvent's polarity results in a decrease in the rate of
S N2 reactions.
 This decrease occurs because protic solvents solvate
the nucleophile, thus lowering its ground state energy.
 Because the energy of the activated complex is a fixed
value, the energy of activation becomes greater and,
therefore, the rate of reaction decreases.

42
Polar aprotic solvents (solvents that
cannot form hydrogen bonds in solution)
do not solvate the nucleophile but rather
surround the accompanying cation,
thereby raising the ground state energy of
the nucleophile.
Because the energy of the activated
complex is a fixed value, the energy of
activation becomes less and, therefore, the
rate of reaction increases.
43
 Figure below illustrates the effect of solvent polarity on
the energy of activation and, thus, the rate of reaction.

 The smaller activation energy leads to the more rapid

reaction.
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SN1 mechanism
 The second major type of nucleophilic substitution
mechanism is the S N1 mechanism.
 This mechanism proceeds via two steps.
 The first step (the slow step) involves the
breakdown of the alkyl halide into an alkyl
carbocation and a leaving group anion.
 The second step (the fast step) involves the
formation of a bond between the nucleophile and
the alkyl carbocation.
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 Because the activated complex contains only one
species—the alkyl carbocation—the substitution is
considered unimolecular.

46
 Carbocations contain sp 2 hybridized orbitals and thus have
planar structures. S N1 mechanisms proceed via a
carbocation intermediate, so a nucleophile attack is equally
possible from either side of the plane.
 Therefore, a pure, optically active alkyl halide undergoing an
S N1 substitution reaction will generate a racemic mixture as
a product.

47
SN1 versus SN2 Reactions
 Whether an alkyl halide will undergo an S N1 or an
S N2 reaction depends upon a number of factors.
 Some of the more common factors include the
natures of the carbon skeleton, the solvent, the
leaving group, and the nature of the nucleophile.

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Nature of the carbon skeleton
 Only those molecules that form extremely stable cations undergo S N1
mechanisms.
 Normally, only compounds that yield 3° (tertiary) carbonications (or
resonance‐stabilized carbocations) undergo S N1 mechanisms rather than
S N2 mechanisms.
 Carbocations of tertiary alkyl halides not only exhibit stability due to the
inductive effect, but the original molecules exhibit steric hindrance of the rear
lobe of the bonding orbital, which inhibits S N2 mechanisms from occurring.
 Primary alkyl halides, which have little inductive stability of their cations and
exhibit no steric hindrance of the rear lobe of the bonding orbital, generally
undergo S N2 mechanisms.

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Figure below illustrates the tendencies of alkyl halides
toward the two types of substitution mechanisms.

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 Polar protic solvents such as water favor S N1 reactions, which
produce both a cation and an anion during reaction.
 These solvents are capable of stabilizing the charges on the ions
formed during solvation.
 Because S N2 reactions occur via a concerted mechanism (a
mechanism which takes place in one step, with bonds breaking
and forming at the same time) and no ions form, polar protic
solvents would have little effect upon them.
 Solvents with low dielectric constants tend not to stabilize ions
and thus favor S N2 reactions.
 Conversely, solvents of high dielectric constants stabilize ions,
favoring S N1 reactions.

51
In general, good leaving groups are those
capable of forming stable ions or molecules
upon displacement from the original
molecule.
Conversely, poor leaving groups form ions of
poor to moderate stability.
Strong bases, such as OH −, NH 2 −, and
RO −, make poor leaving groups.

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Water, which is less basic than a hydroxide
ion, is a better leaving group.
Poor bases usually make good leaving
groups.
A poor base is an ion or group in which the
electrons are tightly bound to the molecule
due to high electronegativity or resonance.
Some good leaving groups are the sulfate ion
and the p‐toluenesulfonate (tosylate ion).

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 The following list ranks atoms and molecules in order of
their stability as leaving groups, from most to least stable.

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Elimination Reactions
 During an elimination reaction, a bond forms by the
removal of two atoms or groups from the original molecule.
 In most instances, the bond that forms is a π bond.
 Elimination reactions compete with substitution reactions
when alkyl halides react with a nucleophile.

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 The elimination of hydrogen halide (a halogen acid) from
an alkyl halide requires a strong base such as the
alkoxide ion, RO −. Weaker bases such as the OH − ion
give poor yields of elimination product.
 If an alkyl halide contains more than two carbons in its
chain, and the carbon atoms adjacent to the carbon atom
bonded to the halogen each have hydrogen atoms
bonded to them, two products will form.

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 The major product is predicted by Zaitsev's Rule, which
states that the more highly branched alkene will be the
major product.
 For example, in the dehydrohalogenation reaction
between 2‐chlorobutane and sodium methoxide, the
major product is 2‐butene.

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Mechanism of Elimination Reactions
 As noted earlier, the halogen‐carbon bond in an alkyl
halide is polarized due to the electronegativity difference
between the atoms.
 This polarization can lead to the formation of a partial or
fully positive charge on the carbon atom.

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 The full or partial positive charge on the carbon atom is
delocalized (dispersed) down the carbon chain.
 This, in turn, makes the hydrogen atoms attached to
these carbons very slightly positive and thus very
weakly acidic.
 Therefore, a very strong base can now remove a slightly
positive hydrogen with the resulting release of electrons
down the chain, forming a π bond between the carbon
atoms.
 The actual mechanism can be one of two types, E1 or
E2, depending upon the structure of the activated
complex.

59
E1 mechanism
 An atom that bears a pair of unshared electrons
takes on one of two roles.
 The atom may share these electrons with a carbon
atom that bears a leaving group, or it may share
these electrons with a hydrogen atom.
 In the former case, the atom acts as a nucleophile,
while in the latter case it acts as a base.
 Therefore, depending on reaction conditions, the
atom may be involved in a substitution reaction or an
elimination reaction.
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 The reaction of an OH − ion with tertiary butyl bromide leads to little or no
substitution product because steric hindrance blocks the rear lobe of the
carbon atom to which the bromine atom is bonded.
 With the aid of a polar solvent, the bromine‐carbon bond ionizes to form a
tertiary carbocation and a bromide ion.
 The hydrogen atoms on the carbons adjacent to the carbocation carbon
acquire a slight positive charge, allowing the OH − ion to employ its basic
characteristics.
 Thus, the OH − ion abstracts a hydrogen atom, and the electrons migrate
down the chain, forming a double bond.

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The activated complex
for this reaction
contains only the alkyl
halide and is, therefore,
unimolecular.
The reaction follows an
E1 mechanism.

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E2 mechanism
 Elimination reactions can also occur when a carbon
halogen bond does not completely ionize, but merely
becomes polarized.
 As with the E1 reactions, E2 mechanisms occur when the
attacking group displays its basic characteristics rather
than its nucleophilic property.
 The activated complex for this mechanism contains both
the alkyl halide and the alkoxide ion.

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 Following is the complete mechanism for the E2
elimination reaction:

64
Grignard Reaction
 In a Grignard reaction, an alkyl halide reacts with magnesium
metal in an anhydrous ether solvent to create an organometallic
reagent.

 The Grignard reagent is highly reactive and is used to prepare

many functional groups.
 An example is the preparation of a carboxylic acid by reaction
with carbon dioxide and mineral acid.

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Uses of Alkyl Halides

CFCs and their replacements

• CFCs are chlorofluorocarbons - compounds containing
carbon with chlorine and fluorine atoms attached.
• Two common CFCs are:
• CFC-11 (CCl3F)
• CFC-12 (CCl2F2)

66
Uses of CFCs
 CFCs are non-flammable and not very toxic.
 They therefore had a large number of uses.
 They were used as refrigerants, propellants for aerosols, for
generating foamed plastics like expanded polystyrene or
polyurethane foam, and as solvents for dry cleaning and for
general degreasing purposes.
 Unfortunately, CFCs are largely responsible for destroying the
ozone layer.
 In the high atmosphere, the carbon-chlorine bonds break to
give chlorine free radicals.

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Uses of CFCs
 In the high atmosphere, the carbon-chlorine bonds break to give
chlorine free radicals.
 It is these radicals which destroy ozone.
 CFCs are now being replaced by less environmentally harmful
compounds.
 CFCs can also cause global warming.
 One molecule of CFC-11, for example, has a global warming potential
about 5000 times greater than a molecule of carbon dioxide.
 On the other hand, there is far more carbon dioxide in the atmosphere
than CFCs, so global warming isn't the major problem associated with
them.

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Replacements for CFCs
 These are still mainly halogenoalkanes, although simple
alkanes such as butane can be used for some
applications (for example, as aerosol propellants).
 Hydrochlorofluorocarbons (HCFCs): These are carbon
compounds which contain hydrogen as well as halogen
atoms.
 For example: CHClF2

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Hydrochlorofluorocarbons (HCFCs):
The formula can be worked out from the
number in the name in exactly the same way
as for CFCs.
These have a shorter life in the atmosphere
than CFCs, and much of them is destroyed in
the low atmosphere and so doesn't reach the
ozone layer.
HCFC-22 has only about one-twentieth of the
effect on the ozone layer as a typical CFC.
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Hydrofluorocarbons (HFCs): These are
compounds containing only hydrogen and
fluorine attached to carbon.
For example: CH2F-CF3
Because these HCFCs don't contain any
chlorine, they have zero effect on the ozone
layer. HFC-134a is now widely used in
refrigerants, for blowing foamed plastics and
as a propellant in aerosols.
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Hydrocarbons
 These have no effect on the ozone layer, but
they do have a down-side.

 They are highly flammable and are involved in

environmental problems such as the formation
of photochemical smog.

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Other uses of organohalogen compounds
 Strictly speaking, the compounds we are talking about
here are halogenoalkenes, not halogenoalkanes:
 Chloroethene, CH2=CHCl, is used to make
poly(chloroethene) - usually known as PVC.
 Tetrafluoroethene, CF2=CF2, is used to make
poly(tetrafluoroethene) - PTFE.

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Lab uses of halogenoalkanes

Halogenoalkanes with lots of things

leading to a wide range of different
organic products.
Halogenoalkanes are therefore useful in
the lab as intermediates in making other
organic chemicals.

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Uses and Applications:
• Alkyl halides, or haloalkanes, have a wide
range of applications in various fields due to
their unique chemical properties.
• Overall, alkyl halides play a vital role in organic
synthesis, chemical manufacturing, and various
industrial applications, making them essential
compounds in modern chemistry and industry.

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• Organic Synthesis:
–Alkyl halides are important starting
materials in organic synthesis for the
preparation of various organic compounds.
–They serve as key intermediates in the
synthesis of pharmaceuticals,
agrochemicals, polymers, and specialty
chemicals.
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Nucleophilic Substitution Reactions:
• Alkyl halides undergo nucleophilic substitution
reactions, where the halogen atom is replaced
by a nucleophile.
• These reactions are widely used in organic
synthesis to introduce functional groups, such
as hydroxyl (-OH), amino (-NH2), and cyano (-
CN) groups, into organic molecules.
77
Grignard Reactions:
• Alkyl halides react with magnesium metal to
form organo-magnesium compounds known
as Grignard reagents.
• Grignard reagents are versatile intermediates
in organic synthesis and are used to form
carbon-carbon bonds, as well as to prepare
alcohols, ketones, and other functional
groups.
78
Halogenation Reactions:
• Alkyl halides can undergo halogenation
reactions, where additional halogen atoms
are added to the molecule.
• These reactions are used in the production
of specialty chemicals, such as
refrigerants, solvents, and flame
retardants.
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Synthetic Polymers:
• Alkyl halides are used as monomers in the
production of synthetic polymers, such as
polyvinyl chloride (PVC), polytetrafluoroethylene
(PTFE), and polystyrene.
• These polymers have a wide range of
applications in industries such as construction,
automotive, and electronics.
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Solvents:
• Some alkyl halides, such as chloroform and
dichloromethane, are used as solvents in
various industrial processes, including
extraction, cleaning, and degreasing.
• However, their use as solvents is decreasing
due to environmental and health concerns
associated with their toxicity and potential for
environmental pollution. 81
Pharmaceuticals and Agrochemicals:
• Alkyl halides are used in the synthesis of
pharmaceuticals and agrochemicals, including
antibiotics, antiviral drugs, and herbicides.
• They serve as key building blocks in the
synthesis of complex organic molecules with
biological activity.

82
Anesthetic Agents:
• Some alkyl halides, such as chloroform
and halothane, were historically used
as general anesthetic agents.
• However, their use has declined due to
safety concerns and the development
of safer alternatives.
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Model Questions
• Define alkyl halides and provide an example.
• Describe the classification of alkyl halides based on the
number of halogen atoms attached to the alkyl group.
• Explain the general reaction mechanism for the nucleophilic
substitution of alkyl halides.
• How do alkyl halides participate in the Grignard reaction?
Provide an example.
• Discuss the importance of alkyl halides in organic synthesis,
giving examples of their applications.
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Model Questions
• Compare primary, secondary, and tertiary alkyl
halides in terms of reactivity and ease of nucleophilic
substitution reactions.
• Describe the halogenation reaction of alkyl halides
and its significance in organic chemistry.
• Explain the role of alkyl halides in the production of
synthetic polymers. Give examples of polymers
derived from alkyl halides.
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Model Questions
• Discuss the environmental and health
concerns associated with the use of certain
alkyl halides as solvents and anesthetic
agents.
• Provide a brief overview of the historical
and contemporary uses of alkyl halides in
various industries.
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