An elimination reaction is a reaction in which atoms are removed as molecules or compounds. Elimination is generally catalysed by a metal, an acid or base.
Elimination reactions often compete with substitution reactions. In this reaction, a substrate (typically an alkyl halide) eliminates one equivalent (unit) of acid to form an alkene. Two possible mechanisms are available for this elimination reaction – E1 and E2 mechanisms.
Table of Contents
- What is Elimination Reaction?
- Important Methods of Elimination Reaction
- Mechanism Of Elimination Reaction
- E1 Reaction
- E2 Reaction
- Elimination Reaction Example
- Frequently Asked Questions – FAQs
What is Elimination Reaction?
Elimination reaction is a type of reaction that is mainly used to transform saturated compounds (organic compounds which contain single carbon-carbon bonds) to unsaturated compounds (compounds which feature double or triple carbon-carbon bonds).
Besides, it is an important method for the preparation of alkenes.
An elimination reaction is a type of chemical reaction where several atoms either in pairs or groups are removed from a molecule. The removal usually takes place due to the action of acids and bases or the action of metals. It can also happen through the process of heating at high temperatures.
Important Methods of Elimination Reaction
Normally, elimination reactions are distinguished by the kind of atoms or groups of atoms that leave the molecule. Due to this, there are two main methods involved in this type of reaction;
In the dehydration method, there is the elimination of a water molecule mostly from compounds such as alcohol. Sometimes, this method is also called a Beta elimination reaction where the leaving group and H are placed at neighbouring carbon atoms. On the other hand, in dehydrohalogenation, there is a removal of a hydrogen atom and a halogen atom.
Mechanism Of Elimination Reaction
The elimination reaction consists of three fundamental events, and they are;
- Proton removal.
- Formation of C-C pi bond.
- Removal of the leaving group.
Depending on the reaction kinetics, elimination reactions can occur mostly by two mechanisms namely E1 or E2 where E is referred to as elimination and the number represents the molecularity.
- In the E1 mechanism which is also known as unimolecular elimination, there are usually two steps involved – ionization and deprotonation.
- During ionization, there is a formation of carbocation as an intermediate. In deprotonation, a proton is lost by the carbocation.
- This happens in the presence of a base which further leads to the formation of a pi-bond in the molecule.
- In E1, the reaction rate is also proportional to the concentration of the substance to be transformed.
- It exhibits first-order kinetics.
The E1 mechanism shares the features of the SN1 reaction. The initial step is the formation of a carbocation intermediate through the loss of the leaving group. This slow step becomes the rate-determining step for the whole reaction.
- In an E2 mechanism which refers to bimolecular elimination is basically a one-step mechanism.
- Here, the carbon-hydrogen and carbon-halogen bonds mostly break off to form a new double bond.
- However, in the E2 mechanism, a base is part of the rate-determining step and it has a huge influence on the mechanism.
- The reaction rate is mostly proportional to the concentrations of both the eliminating agent and the substrate.
- It exhibits second-order kinetics.
The E2 mechanism can generally be represented as below. In the below-mentioned representation, B stands for base and X stands for halogen.
The rate of the E2 reaction is
Rate = k[RX][Base]
So the reaction rate depends on both the substrate (RX) and the base involved. In the elimination reaction, the major product formed is the most stable alkene.
Elimination Reaction Example
One of the common examples of elimination reaction is the dehydration of alcohol. Here the process takes place in the presence of a base such as an ethoxide ion (C2H5O–). It can be represented as;
“E2 and E1 reactions differ significantly in the nature of the transition states that determine the regiochemistry of the product”. The E2 pathway involves a transition state leading from starting material directly to the product. The product forming step of an E1 reaction is more exothermic than that of an E2 reaction. Thus, the E1 reaction has a relatively early transition state, closely resembling the carbocation formed in the rate-determining step.
Frequently Asked Questions – FAQs
What happens in an elimination reaction?
An elimination reaction is a form of organic reaction in which in either a one- or two-step process two substituents are separated from a molecule.
What is nucleophilic elimination reaction?
Nucleophilic substitution is a fundamental class of reactions in which an electron-rich nucleophile selectively binds or attacks the positive or partially positive charge of an atom or group of atoms as a substitute for a so-called leaving group.
What is the difference between substitution and elimination reactions?
Substitution reaction involves the replacement of a particular atom or group with another group. An elimination reaction involves the removal of a group or atom.
What factors affect elimination reactions?
The stability of the carbocation, the form of the leaving group, and the solvent type are the three essential factors that influence E1 elimination reactions.
Why is alcohol used in elimination reactions?
Most alcohols are weaker acids than water because of which equilibrium lies to the left. Hydroxyl ions and a proton from alcohol are removed as water molecules here. Water is a better leaving group than -OH.
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