Question:
Which of the following sequence of reactions is suitable to synthesize chlorobenzene?
Which of the following sequence of reactions is suitable to synthesize chlorobenzene?
Updated On: May 2, 2025
- Benzene, Cl2, anhydrous FeCl3
- Phenol, NaNO2, HCl, CuCl
HCl
HCl, Heating
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The Correct Option is A
Approach Solution - 1
To synthesize chlorobenzene, we need to understand the process involving benzene and chlorine. This reaction is known as an electrophilic aromatic substitution. The sequence of reactions suitable for this synthesis involves:
- Benzene (C6H6), Cl2, and anhydrous FeCl3:In this reaction, benzene reacts with chlorine in the presence of anhydrous iron(III) chloride (FeCl3) as a catalyst.
The mechanism is as follows:
- Formation of the electrophile:FeCl3, being a Lewis acid, facilitates the formation of the chloronium ion (Cl+) from Cl2.
- Attack by benzene:The π-electrons of the benzene ring attack the Cl+ ion, forming a sigma complex.
- Deprotonation:The complex loses a hydrogen ion (H+), reforming the aromatic ring and yielding chlorobenzene.
The overall equation for the reaction is:
C6H6 + Cl2 → C6H5Cl + HCl
Thus, the sequence of:
Benzene, Cl2, and anhydrous FeCl3 is used for the synthesis of chlorobenzene.
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The correct option is (A): Benzene, Cl2, anhydrous FeCl3
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Concepts Used:
Haloalkanes and Haloarenes
The hydrocarbons such as Haloalkanes and Haloarenes are the ones, in which one or more hydrogen atoms are replaced with halogen atoms. The main difference between Haloalkanes and Haloarenes is that Haloalkanes are derived from open chained hydrocarbons, also called alkanes, and Haloarenes are derived from aromatic hydrocarbons.
- Haloalkanes have hydrocarbons made up of aliphatic alkanes and one or more hydrogen atoms replaced by halogens (elements such as Chlorine, Bromine, Fluorine, Iodine, etc.) whereas, haloarenes consist of aromatic ring or rings and one or more hydrogen atoms replaced by halogens.
- In haloalkanes, the halogen atom is attached to the sp3 hybridized carbon atom of the alkyl group whereas, in haloarenes, the halogen atom is attached to the sp3 hybridized carbon atom of the alkyl group.
- Haloalkanes are saturated organic compounds where all the chemical bonds are attached to the carbon atom with single bonds and a single carbon atom is attached to the Halogen atom, whereas, the haloarenes differ from Haloalkanes by their method of preparation and properties.
- Haloalkanes are made by aliphatic alkanes by the process of free radical halogenation, whereas, haloarenes are made by direct halogenation of aromatic rings.
- Haloalkanes are odorless compounds, whereas, haloarenes have a sweet odor.
- Haloalkanes precipitate in SN2 substitution reactions, whereas, haloarenes do not precipitate in SN2 substitution reactions.
- Example of haloalkanes is CH3Cl (Methyl Chloride) and CH3CH2Br (Ethyl Bromide) and the example of haloarenes is Chlorobenzene, Bromobenzene.