What is a Reaction Mechanism?

In organic chemistry, the mechanism of an organic reaction is defined as a complete step-by-step explanation of how a reaction of organic compounds happens. A completely detailed mechanism would relate the first structure of the reactants with the last structure of the products and would represent changes in structure and energy all through the reaction step.

Nucleophilic Substitution Reaction

The figure shows the nucleophilic substitution reactions

The mechanism of SN2 incorporates the nucleophilic substitution and leaving of the functional group. The leaving group for the most part includes halides or other electron-withdrawing groups with a nucleophile. A bimolecular substitution reaction happens when the carbon particle at the center is viably available to the nucleophile attack. In SN2, there are a few conditions that impact the rate of the reaction. In bimolecular substitution reactions, there are two groupings of substances that impact the rate of reaction: substrate and nucleophile. The rate condition for this reaction would be Rate=k [Sub][Nuc].

By contrast, a unimolecular substitution reaction incorporates two phases. The SN1 reaction happens when the carbon molecule of the substrate is enclosed by bulky groups because such groups interfere sterically with the SN2 reaction considering the way that a highly substituted carbon forms a steady carbocation. The rate of unimolecular reactions mostly depends on the concentration of only one substrate. The rate condition for this would be Rate=k [Sub].

The diagram shows the mechanisms of both unimolecular and bimolecular reaction

Electrophilic Substitution Reaction

An elimination reaction is a reaction wherein one group connected to a compound is replaced by an electrophile.

The figure shows electrophilic substitution reaction

Here, the chlorine cation goes about as an electrophile and replaces a hydrogen atom in the benzene ring. The products shaped in this electrophilic substitution reaction incorporate a proton and chlorobenzene.

Electrophilic Aromatic Substitution Reaction

In aromatic substitution reactions, a particle joined to a ring is substituted with an electrophile. Instances of such reactions incorporate aromatic sulfonation, Friedel-crafts reactions, etc. These reactions can be utilized to acquire aryl halides from aromatic rings and halogens.

Electrophilic Aliphatic Substitution Reaction

In electrophilic aliphatic substitution reactions, an electrophile replaces the functional group in an aliphatic compound. These reactions can be characterized into the accompanying five sorts:

  • Halogenation of ketones
  • Nitrosation
  • Keto-enol tautomerism
  • Inclusion of a carbene into a carbon-hydrogen bond
  • Diazonium coupling (aliphatic)

Mechanism of Electrophilic Substitution Reaction

The mechanism of electrophilic substitution reaction includes three stages.

Stage 1: Generation of Electrophile

The electrophiles are generated from the chlorination, alkylation, and acylation of an aromatic ring using an extremely valuable lewis acid anhydrous aluminum chloride.

The figure shows the generation of electrophile

Stage 2: Formation of Carbocation

The electrophile attacks the aromatic rings and forms a sigma bond or an arenium particle.

The diagram shows the electrophilic attack

Through resonance structure, these arenium particles attain their stability. Since the delocalization of electrons stops at the sp3 hybridized carbon, the sigma bond or the arenium particle loses its aromatic nature.

The diagram shows the delocalization of electrons over resonance structure

Stage 3: Removal of Proton

To reestablish the aromaticity, the sigma bonds set a proton free from the sp3 hybridized carbon when it is attacked by the [AlCl4]. The reaction portraying the expulsion of a proton from the sigma complex is given here:

The reaction portrays the expulsion of a proton from the sigma complex .

Consequently, the electrophile replaces the hydrogen particle in the benzene ring. The electrophilic substitution reaction is vital in organic chemistry, as the idea is utilized in numerous organic naming reactions.

Elimination Reaction

In an elimination reaction, a substrate, regularly an alkyl halide, neutralizes an acid to form an alkene. Two potential systems accessible for these elimination reactions are unimolecular and bimolecular mechanisms. Normally, elimination reactions are recognized by the sort of groups or atoms that leave the atom. Because of this, there are two fundamental techniques associated with this sort of reaction:

  • Dehydration
  • Dehydrohalogenation

In the dehydration technique, the H2O atom is eliminated from compounds like alcohol. Now and again, this technique is likewise called beta elimination reaction where the leaving group and hydrogen are put at neighbor carbon molecules. Then again, in dehydrohalogenation, there is an expulsion of a hydrogen particle and a halogen.

The diagram gives the example of elimination reaction

Components of Elimination Reaction

The elimination comprises three major occasions, and they are:

  • Proton expulsion
  • C-C pi bond is shaped
  • There is a breakage in the obligation of the leaving group

Unimolecular Elimination (E1 Reaction)

An E1 reaction, otherwise called unimolecular elimination, normally includes two stages – ionization and deprotonation. During ionization, there is an arrangement of carbocation as a moderate. In deprotonation, a proton is lost by the carbocation. This occurs within the sight of a base, which further prompts the arrangement of a pi-bond in the particle. In a unimolecular elimination reaction, the reaction rate is likewise relative to the centralization of the substance to be changed.

The unimolecular elimination mechanism shares the provisions of the unimolecular substitution reaction. The underlying advance is the development of carbocation middle through the deficiency of the leaving group. This slow step turns into the rate-deciding step for the entire reaction.

The diagram shows the mechanism of unimolecular elimination reaction

Bimolecular Elimination (E2 Reaction)

An E2 component that alludes to bimolecular elimination is essentially a one-step mechanism. Here, the carbon-hydrogen and carbon-halogen bonds generally break to form another double bond. Nonetheless, in the bimolecular elimination system, a base is important for the rate-deciding step and it impacts the component. The reaction rate for the most part corresponds to the centralizations of both the particles that get eliminated and the substrate.

The rate of the bimolecular elimination reaction is,

Rate = k [RX][Base]

The diagram shows the mechanisms of bimolecular reaction

Context and Applications

This topic is significant for both undergraduate and postgraduate courses, especially for Bachelors and Masters in Chemistry.

Practice Problems

1. Consider the reaction of tert-butyl chloride with iodide particle:

(CH3)3C Cl + I (CH3)3C I + Cl

If the grouping of iodide particles is multiplied, the rate of formation of tert-butyl iodide will:

a. Double
b. Increase multiple times
c. Remain something similar
d. Decrease

Answer: c

Explanation: In the unimolecular substitution reaction, the rate is autonomous of the nucleophile involved since the nucleophile isn't associated with the rate-deciding step.

2. Which of the accompanying alkyl halides would you hope to go through SN1 reaction most quickly?

a. CH3CH2CH2CH2CH2 Br b. CH3CH2CH2CH (CH3) Br  c. CH3CH2C (CH3)2 Br
d. They won't go through SN1 response

Answer: c

Explanation: For a unimolecular substitution reaction, the leaving group leaves before the formation of a bond. In this way, a carbocation is formed as an intermediate, which is the steadiest one tertiary carbon.

3. Which of the accompanying alkyl halides would you hope to give the best return of replacement product (SN2) with CH3CH2O-Na+?

a. CH3CH2CH2CH2CH2 Br b. CH3CH2CH2CH (CH3) Br c. CH3CH2C (CH3)2 Br
d. They will give the same yield of replacement items

Answer: a

Explanation: For a bimolecular substitution reaction, the nucleophile needs to attack from the rear of the leaving group. Hence the carbon being attacked should not be sterically ruined, in any case, the end will contend.

4. Primary alcohols undergo what type of reaction to form alkenes?

a. Elimination
b. Oxidation
c. Reduction
d. Hydrolysis

Answer: a

Explanation: The primary alcohols are converted to alkenes upon elimination reaction.

5. Which one of the following will not come under the organic addition reaction?

a. Hydration
b. Dehydration
c. Halogenation
d. Hydrohalogenation

Answer: b

Explanation: We know that dehydration is an elimination reaction and therefore it is not an addition reaction.

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