Which one of the following chlorohydrocarbons readily undergoes solvolysis?
- $CH_2 = CHCl$
The Correct Option is C
Approach Solution - 1
Correct Answer: Compound C
Explanation:
Solvolysis, particularly via the SN1 mechanism, involves the formation of a carbocation intermediate. The stability of this carbocation significantly influences the reaction rate; more stable carbocations lead to faster solvolysis.
Among the given compounds:
- Compound C: This is benzyl chloride (C6H5CH2Cl). Upon ionization, it forms a benzyl carbocation (C6H5CH2+), which is highly stabilized due to resonance with the aromatic ring.
- Other Compounds: Without specific structures provided, it's generally observed that alkyl chlorides without resonance stabilization form less stable carbocations compared to benzyl chloride.
Due to the resonance stabilization of the benzyl carbocation, Compound C (benzyl chloride) undergoes solvolysis more readily than the others.
Solvolysis is related to stability of carbocation formed and among these benzyl carbocation is most stable. So, it will undergo solvolysis readily.
Approach Solution -2
Solvolysis is a type of nucleophilic substitution (SN1) reaction where the solvent acts as the nucleophile. The rate of solvolysis depends on the stability of the carbocation formed during the reaction. More stable carbocations lead to faster solvolysis.
Let's analyze each option:
Option(1):
This compound would form a primary carbocation. Primary carbocations are relatively unstable.
Option(2):
This compound would form a secondary carbocation. Secondary carbocations are more stable than primary carbocations.
Option(3):
This compound would form a tertiary carbocation. Tertiary carbocations are the most stable among primary, secondary, and tertiary due to hyperconjugation and inductive effects.
Option(4):
This compound would form a primary carbocation. The carbocation is also allylic, which adds some stability due to resonance. However, tertiary carbocations are still more stable.
Comparing all the options, the compound that forms the most stable carbocation (tertiary) will undergo solvolysis most readily.
Therefore, the correct answer is: Option(3)
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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.