CHM 224(GROUP 2)

PRESENTATION ON
ELIMINATION REACTION

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 CONTENTS
 Introduction to the topic; elimination reaction
 Examples of elimination reactions and the techniques for studying this
reaction
 Types of elimination reactions
 Mechanism of this reaction
 Factors affecting this reaction
 Applications of these reactions and the recent improvements and
advancements in the reaction.
 Reagents and catalysts for promoting this reaction
 Summary
 References.
Introduction To Elimination Reaction
Elimination reactions are fundamental chemical transformations in which a molecule
loses atoms or groups of atoms to form a new product. It is characterized by the removal
of substituents from a molecule, leading to the formation of a double or triple bond.
The atoms or groups of atoms that are removed are typically hydrogen atoms; although
other atoms or groups can also be eliminated.
The history of the elimination reaction dates back to the early 1800s, when French
chemist Edmond Frémy first observed the formation of unsaturated hydrocarbons from
the dehydration of alcohols. However, it wasn't until the late 1800s that German chemist
August Kekulé proposed the mechanism for this reaction. Kekulé proposed that the
elimination reaction involved the removal of a hydrogen atom and a hydroxyl group
from the alcohol molecule, leaving behind a carbon-carbon double bond. In the early
1900s,the mechanism for elimination reactions was further refined by other chemists,
such as Robert Robinson and Otto Hahn.
There are a wide variety of compounds that can undergo elimination reactions. Some
common examples include alcohols, alkenes, and aldehydes. Alcohols are particularly
prone to elimination reactions, as they contain a hydroxyl group that can easily be
removed. For example, the elimination reaction of ethanol produces ethene. Alkenes
also undergo elimination reactions, and they can produce a variety of unsaturated
hydrocarbons as products. For example, the elimination reaction of 2-butene produces
2-butyne.
Introduction To Elimination
Reaction(cont'd)
The specific chemical configuration of a molecule can greatly affect the outcome of an
elimination reaction. The presence of a beta hydrogen atom is often required for an
elimination reaction to take place. A beta hydrogen atom is adjacent to a carbon-carbon
double bond. In addition, the stability of the resulting product is also important.
Generally, the more stable the product, the more likely it is to form. For example, in the
case of ethanol, the resulting product, ethene, is a very stable molecule due to its alkene
structure.
An elimination reaction is similar to other organic reactions, such as substitution
reactions and addition reactions. However, there are some key differences between these
types of reactions. In a substitution reaction, a new atom or group of atoms replaces an
existing atom or group of atoms in a molecule. In an addition reaction, a new atom or
group of atoms is added to a molecule. In an elimination reaction, a molecule is
"simplified" by the removal of atoms or groups of atoms. In terms of products,
elimination reactions typically produce unsaturated hydrocarbons, while substitution
and addition reactions can produce a variety of different products .
Examples Of Elimination Reaction
Elimination reactions are a class of organic reactions where a molecule loses atoms or
groups of atoms to form a double bond or a triple bond. These reactions involve the
removal of two substituents from a molecule to generate a new unsaturated compound.
There are several different techniques used to perform elimination reactions, each with
its own specific conditions and requirements. Here are some of the commonly used
techniques:
1. Dehydration: Dehydration is the elimination of water from a molecule. It is typically
carried out by heating an alcohol in the presence of a strong acid catalyst, such as
sulfuric acid (H2SO4) or phosphoric acid (H3PO4). The acid protonates (the addition
of a proton (H+) to a molecule or an atom within a molecule) the alcohol, making it a
better leaving group, and then the leaving group (a water molecule) is eliminated to
form an alkene. For example:
CH3CH2OH (ethanol) + H2SO4 (sulphuric acid)→ CH2=CH2 (ethylene) + H2O

In this example, ethanol is dehydrated to form ethylene.

Examples Of Elimination
Reaction(cont'd)
Compounds that possess an alcohol functional group can undergo dehydration reactions. For instance,
ethanol(CH3CH2OH) can undergo dehydration because it contains the alcohol group (OH),
which is the leaving group in this reaction. Compounds that do not possess the alcohol group,
such as alkanes, cannot undergo this reaction
2. Dehydrohalogenation: Dehydrohalogenation involves the removal of a hydrogen halide (such as
HCl, HBr, or HI) from a molecule to form an alkene. It is typically performed by treating an alkyl
halide with a strong base, such as sodium hydroxide (NaOH) or potassium hydroxide (KOH).
For example: CH3CH2Br (bromoethane) + KOH → CH2=CH2 (ethylene) + KBr + H2O

In this example, bromoethane undergoes dehydrohalogenation to form ethylene.

Compounds that possess an alkyl halide can undergo dehydrohalogenation reactions. For example
bromoethane(CH3CH2Br) can undergo this reaction because it contains the alkyl halide group.
Compounds that do not possess an alkyl halide group, such as alcohols, cannot undergo this
reaction.
Examples Of Elimination
Reactions(cont'd)
3. β-Elimination: β-Elimination is a type of elimination reaction where a leaving group
and a hydrogen atom are removed from adjacent carbon atoms. It is commonly
observed in compounds with leaving groups on adjacent carbons, such as dihalides,
haloalcohols, or haloamines. β-Elimination reactions can be performed using various
reagents and conditions depending on the specific compound and desired product. An
example of β-elimination is the dehydrohalogenation of 2-bromopropane:
CH3CHBrCH3 (2-bromopropane) + KOH → CH2=CH2 (ethylene) + KBr + H2O .
In this case, 2-bromopropane undergoes β-elimination to form ethylene. Compounds
with leaving groups(the atom or group of atoms that departs from the molecule,
typically taking with it a pair of electrons) on adjacent carbons, such as 2-
bromopropane, can undergo β-elimination reactions. Compounds that do not have
such cannot undergo this reaction.
Types of Elimination Reaction
There are two main types of elimination reaction namely:
 E1
 E2

 E1 reactions are those elimination reactions which take place by two steps and are unimolecular. In E1 reactions,
E stands for elimination while 1 stands for its unimolecular nature. Unimolecular means its rate of reaction
depends on one molecule or its order of reaction is 1. It is a two-step process of elimination: Formation of
carbocation(ionisation) and deprotonation. The rate of reaction depends on only one molecule or reactant, so it
is of 1st order kinetics. The reaction is endothermic and occurs at high temperature. The reaction occurs in the
presence of weak bases only. In this reaction, polar protic solvent such as H2O is used. E1 reactions take place
with tertiary alkyl halides, secondary alkyl halides and alcohols. It follows the Saytzeff rule otherwised spelt as
Zaitsev's Rule when small base attacks which states that when there is more than one possible beta carbon that
can be deprotonated while performing an elimination reaction, the more substituted one (the one with fewer
hydrogen atoms attached) is preferred. Deprotonating the more substituted beta carbon will lead to a more
substituted alkene. And a more substituted alkene is a more stable alkene, this is ultimately the reasoning behind
Zaitsev's Rule. There are two beta carbons: one secondary and one primary. Zaitsev's Rule predicts that the
alkene formed when deprotonating the secondary carbon will be the major product (referred to as the Zaitsev
product) whereas the alkene formed when deprotonating the primary carbon will be a minor product (referred to
as the Hofmann or anti-Zaitsev product).
Types of Elimination Reactions(cont'd)
 E2 reactions are those elimination reactions which take place by single step and are
bimolecular. In E2 reactions, E stands for elimination while 2 stands for its bimolecular
nature. Bimolecular means its rate of reaction depends on two reactants (or two
molecules) or its order of reaction is 2. Few specific points about E2 reactions are: It is a
single step process of elimination; Ionisation and deprotonation takes place
simultaneously. The rate of reaction depends on only two molecules or reactants. So, it is
of 2nd order kinetics. The reaction is endothermic and occurs at high temperature like E1
reactions. The reaction occurs in the presence of a strong base only. In this reaction, the
polar aprotic solvent is used. E2 reactions take place by the formation of a transition
state. As the reaction involves only one step, so is the rate-determining step. E2 reactions
take place mainly with primary substituted alkyl halides and secondary alkyl halides. In
the E2 reaction, the formation of the pi bond takes place. In E2 reactions, the base must
be strong enough to remove a weakly acidic hydrogen. In the reaction for the formation of
the pi bond, the hybridization of carbons needs to be lowered from sp3 to sp2. It also
follows the Saytzeff rule.
Mechanism of Elimination reaction
Elimination reactions are a fundamental process in organic chemistry where atoms or a
group of atoms are removed from a molecule to create a double or triple carbon-carbon
bond. This reaction can occur through two main mechanisms: E1 and E2.
 E1 (Unimolecular) Mechanism:
This is a two-step process favored by tertiary alkyl halides (compounds with a carbon
bonded to three other carbons and a halogen) and can occur in acidic conditions or with
weak bases.
 Step 1: Ionization: The C-X bond (where X is an halogen like chlorine or bromine) also
known as the leaving group breaks and departs first taking a bonding electron with it,
forming a carbocation (a positively charged carbon ion with only three attached group)
and a halide ion.
This step is slow and rate-determining, meaning it controls the overall reaction speed.
 Step 2: Deprotonation: A base (even a weak base like water in some cases) removes a
proton (H+) from a nearby carbon (usually the β-carbon, adjacent to the carbocation).
This carbon losing the proton and the one that lost the leaving group form a new pi bond,
resulting in the final alkene product.
Mechanism of Elimination
Reaction(Cont'd)
E2 (Bimolecular) Mechanism:
This is a one-step process that's faster than E1 and is favored by secondary alkyl
halides (compounds with a carbon bonded to two other carbons) and strong bases.
In this mechanism, the elimination and deprotonation steps occur simultaneously.
The base abstracts a proton from the β-carbon(i.e the carbon beside/adjacent to the
carbon that lost the leaving group) simultaneously as the leaving group departs. This
often requires a strong base. This carbon losing the proton and the one that lost the
leaving group form a new pi bond, resulting in the final alkene product.
Factors affecting elimination reaction
Elimination reactions in chemistry can be influenced by several factors:
1. Substrate structure: The structure of the substrate molecule affects the ease of
elimination. Substrates with bulky groups hinder elimination, while those with smaller
substituents generally favor it.
2. Nature of the leaving group: The ability of the leaving group to depart influences the
reaction rate. Good leaving groups facilitate elimination reactions.
3. Temperature: Higher temperatures generally increase the rate of elimination reactions
by providing more kinetic energy to the reacting molecules.
4. Concentration: Higher concentrations of reactants typically increase the rate of reaction
by increasing the frequency of molecular collisions.
5. Solvent: The choice of solvent can affect the rate and selectivity of elimination reactions.
Polar solvents can stabilize charged intermediates, while nonpolar solvents can favor
reactions involving nonpolar intermediates.
6. Presence of catalysts: Certain catalysts can accelerate elimination reactions by providing
an alternative reaction pathway with lower activation energy.
Applications of Elimination Reactions
Elimination reactions are applied in various fields, including:
1. Pharmaceutical industry: Elimination reactions are crucial in organic synthesis to create
specific molecules, such as pharmaceutical drugs. For example, the synthesis of certain
drugs involves elimination reactions to form desired functional groups.
2. Petrochemical industry: In refining crude oil, elimination reactions are utilized to convert
certain hydrocarbons into more valuable products like gasoline, diesel, and lubricants.
3. Polymer chemistry: Elimination reactions play a role in the production of polymers, where
monomers undergo elimination reactions to form polymer chains.
4. Environmental science: Elimination reactions are involved in various environmental
processes, such as the breakdown of pollutants and toxins in soil and water through
natural degradation pathways.
5. Biochemistry: Enzymatic elimination reactions are essential in biological processes,
including the metabolism of drugs and toxins in the human body.These are just a few
examples, but elimination reactions have wide-ranging applications across industries and
scientific disciplines.
6. Food industry: Elimination reactions are utilized in food processing, such as the
conversion of raw ingredients into finished products through various chemical
transformations, including elimination reactions to create flavor compounds,
preservatives, and colorants.
Applications of Elimination
Reactions(cont'd)
7. Material science: In the production of materials like plastics, elimination reactions are
involved in the synthesis of polymers, allowing for the manipulation of material
properties such as strength, flexibility, and thermal stability.
8. Agricultural chemistry: Elimination reactions are used in the development of
agrochemicals, such as herbicides and pesticides, to selectively target and eliminate
unwanted pests or weeds while minimizing environmental impact.
9. Energy production: In the production of biofuels and renewable energy sources,
elimination reactions can be employed in the conversion of biomass or other organic
materials into fuels like ethanol or biodiesel.
10. Chemical manufacturing: Elimination reactions are integral to the production of a wide
range of industrial chemicals and materials, including solvents, detergents, plastics, and
specialty chemicals used in various manufacturing processes.
11. Environmental remediation: Elimination reactions are utilized in environmental cleanup
efforts, such as the treatment of contaminated soil and groundwater through processes
like bioremediation, where microorganisms break down pollutants via elimination
reactions.
12. Textile industry: In textile manufacturing, elimination reactions are involved in dyeing
processes, where reactive dyes form covalent bonds with fibers through elimination
reactions, resulting in vibrant and colorfast textiles.
 Recent Improvements On Elimination
Reactions
1. Catalysis: Development of new catalysts has enabled more efficient and selective
elimination reactions, reducing the need for harsh reaction conditions and improving
yields. Catalysts such as transition metal complexes, organocatalysts, and biocatalysts have
been explored for their ability to promote various elimination reactions.
2. Stereochemistry control: Researchers have made progress in controlling the
stereochemistry of elimination reactions, allowing for the selective formation of specific
stereoisomers. This advancement is particularly valuable in the synthesis of complex
molecules, including pharmaceuticals and natural products.
3. Green chemistry: Efforts to develop greener and more sustainable elimination reactions
have led to the discovery of new reaction conditions that minimize waste generation,
reduce energy consumption, and utilize more benign solvents and reagents. These
developments align with the principles of green chemistry and contribute to
environmentally friendly synthetic methodologies.
Recent Improvements On Elimination
Reactions(cont'd)
4. Mechanistic understanding: Advances in mechanistic studies have provided deeper
insights into the underlying pathways and kinetics of elimination reactions. This improved
understanding has facilitated the design of more efficient reaction protocols and the
development of new strategies for controlling reaction outcomes.
5. Computational methods: Computational chemistry approaches, such as density functional
theory (DFT) calculations and molecular modeling, have been instrumental in predicting
reaction mechanisms, optimizing reaction conditions, and designing new catalysts for
elimination reactions. These computational tools complement experimental efforts and
accelerate the discovery of novel reactions and reaction pathways.
6. Cross-coupling strategies: Integration of elimination reactions with other synthetic
transformations, such as cross-coupling reactions, has expanded the synthetic toolbox and
enabled the construction of complex molecular scaffolds with higher efficiency and atom
economy
These recent improvements in elimination reactions have enhanced their synthetic
utility, enabling more sustainable and versatile approaches to molecule synthesis across
various disciplines.
Reagents and Catalysts for promoting Elimination
Reaction
The reagents and catalysts used to promote elimination reactions depend on the specific
type of elimination reaction (E1 or E2) and the substrate involved. Here are some
examples:
For E1 Reactions (Unimolecular Elimination):
1. Weak Base: Since E1 reactions proceed through a carbocation(an ion with a positively
charged carbon atom. Among the simplest examples are the methenium CH⁺₃,
methanium CH⁺₅ and vinyl C₂H⁺₃ cations.) intermediate, a weak base is typically used
to abstract a proton in the deprotonation step. Common weak bases include polar
protic solvents such as water (H2O) or alcohols (ROH).
2. Heat: E1 reactions are often carried out under elevated temperatures to provide the
necessary activation energy for the initial step involving carbocation formation.

Note: A polar protic solvent is a solvent that has a hydrogen atom bound to an
electronegative atom, such as oxygen or nitrogen.
Reagents and Catalysts for promoting
Elimination Reaction(cont'd)
For E2 Reactions (Bimolecular Elimination):
1. Strong Base: E2 reactions proceed via a concerted mechanism where the base abstracts a proton
while the leaving group departs. Therefore, a strong base is required to facilitate this step.
Common strong bases include alkoxides (RO⁻) such as potassium tert-butoxide (KOtBu) or
sodium ethoxide (NaOEt), as well as other strong bases like hydroxide ion (OH⁻).
2. Polar Aprotic Solvent: Since E2 reactions occur via a bimolecular mechanism, polar aprotic
solvents are often used to solvate the reactants while minimizing interference with the reaction.
Examples include dimethyl sulfoxide (DMSO), acetone, and acetonitrile.
3. Higher Temperatures: While not always necessary, E2 reactions may be accelerated by higher
temperatures to provide the necessary energy for the reaction to occur efficiently.
In some cases, catalysts may be employed to enhance the rate of elimination reactions. For example,
transition metal catalysts may be used in certain E2 reactions to facilitate proton abstraction or
promote the leaving group's departure.- The choice of reagents and conditions depends on factors
such as the substrate's structure, the desired product, and the reaction kinetics.
Note:
In chemistry, a concerted reaction is a chemical reaction in which all bond breaking and bond making
occurs in a single step.
Solvate: to dissolve a solute in a solvent to form a solution.
Polar aprotic solvent: Polar aprotic solvents are those that are unable to form hydrogen bonds with the
substrate. They have no hydrogen atoms that are directly connected to an electronegative atom.
 Summary
Elimination reactions involve the removal of elements from a molecule to form a
double bond or a ring, have a rich history dating back to the early 19th century. They are
distinct from substitution reactions, which involve the replacement of an atom or group
within a molecule. Elimination reactions play a crucial role in organic synthesis and are
studied using techniques such as spectroscopic methods and kinetic studies. Elimination
reactions can be categorized into E1, E2, and E1cb mechanisms. E1 reactions proceed via a
carbocation intermediate, E2 reactions involve a concerted one-step process, and E1cb
reactions combine elements of both E1 and E2 mechanisms. Examples of elimination
reactions include the dehydrohalogenation of alkyl halides and the dehydration of
alcohols. The mechanism of elimination reactions involves several steps, starting with the
formation of a carbocation or carbanion intermediate, followed by the removal of a
leaving group and the formation of a double bond or ring. The specific steps and events
vary depending on the type of elimination reaction. Numerous factors influence
elimination reactions, including the nature of the substrate, the strength of the base,
steric hindrance, solvent effects, and temperature. Understanding these factors is crucial
for predicting reaction outcomes and optimizing reaction conditions.
 Summary
Elimination reactions find wide applications in organic synthesis, pharmaceuticals, and
materials science. Recent advancements in the field have focused on developing more
efficient and selective methods for conducting elimination reactions, leading to improved
yields and reduced by-products.Reagents and catalysts play a vital role in promoting
elimination reactions by facilitating the removal of elements and controlling reaction
pathways. Common reagents include strong bases like alkoxides and catalysts such as
acids or transition metals, which influence the reaction by stabilizing intermediates or
accelerating specific steps in the mechanism. Understanding the role of reagents and
catalysts is essential for designing effective elimination reactions.
References
 March, J. (2007). Advanced Organic Chemistry: Reactions, Mechanisms, and
Structure. Wiley
 Carey, F. A., & Sundberg, R. J. (2007). Advanced Organic Chemistry Part A:
Structure and Mechanisms. Springer.
 Smith, M. B., & March, J. (2007). March's Advanced Organic Chemistry:
Reactions, Mechanisms, and Structure. Wiley.
 Clayden, J., Greeves, N., Warren, S., & Wothers, P. (2012). Organic Chemistry.
Oxford University Press.