Statement I: High concentration of strong nucleophilic reagent with secondary alkyl halides which do not have bulky substituents will follow \(S_N2\) mechanism.
Statement II: A secondary alkyl halide when treated with a large excess of ethanol follows \(S_N1\) mechanism.
In the light of the above statements, choose the most appropriate from the questions given below:
Statement I: High concentration of strong nucleophilic reagent with secondary alkyl halides which do not have bulky substituents will follow \(S_N2\) mechanism.
Statement II: A secondary alkyl halide when treated with a large excess of ethanol follows \(S_N1\) mechanism.
In the light of the above statements, choose the most appropriate from the questions given below:
- Both statements are true
- Statement I is true, II is false
- Both statements are false
- Statement I is false, Statement II is true
The Correct Option is A
Solution and Explanation
Analysis of Statement I: SN2 reactions are characterized by a single concerted step where the nucleophile attacks the substrate from the opposite side of the leaving group. High concentration of a strong nucleophile enhances the rate of SN2 reactions, especially with secondary alkyl halides that are not hindered by bulky substituents. Thus, Statement I is true.
Analysis of Statement II: SN1 reactions occur in two steps: formation of a carbocation intermediate followed by nucleophilic attack. Secondary alkyl halides can undergo SN1 reactions in the presence of polar protic solvents like ethanol. A large excess of ethanol serves as a nucleophile and stabilizes the carbocation, favoring the SN1 mechanism. Thus, Statement II is also true.
Therefore, both statements are correct: Both Statement I and Statement II are true.
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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.