Which of the following is least reactive towards Sn1 reactions?
C6H5CH2Cl
C6H5Cl
H2C = CH - CH2CL
(C6H5)2 CHCl
The Correct Option is B
Solution and Explanation
Step 1: Understand the Mechanism of SN1 Reactions:
The SN1 reaction mechanism involves the formation of a carbocation intermediate after the leaving group (such as chlorine) departs. The rate-determining step is the departure of the leaving group, and the stability of the carbocation plays a significant role in the reactivity of the compound in an SN1 reaction.
Step 2: Analyze the Structures of the Compounds:
Let's examine each compound to determine which is least reactive in SN1 reactions, which are favored by the formation of stable carbocations:
- C6H5CH2Cl: This is a benzyl chloride. In this case, the carbocation formed after the departure of the chloride ion is a benzyl carbocation, which is highly stabilized by resonance. Therefore, this compound is highly reactive in SN1 reactions.
- C6H5Cl: This is a phenyl chloride. The carbocation formed would be a phenyl carbocation, which is not stabilized by resonance as much as the benzyl carbocation. This makes phenyl chloride less reactive in SN1 reactions compared to benzyl chloride. This is the correct answer, as it is least reactive in SN1 reactions.
- H2C=CH-CH2Cl: This is allyl chloride. The carbocation formed after chloride departure is an allyl carbocation, which is stabilized by resonance, making this compound quite reactive in SN1 reactions.
- (C6H5)2CHCl: This is a benzylic chloride with a bulky group. The carbocation formed is stabilized by both the aromatic ring and the two attached phenyl groups, making this compound reactive in SN1 reactions.
Final Answer:
The least reactive compound towards SN1 reactions is C6H5Cl (phenyl chloride).
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Concepts Used:
Introduction to Organic Chemistry
Organic chemistry is the branch of chemistry that involves the scientific study of organic compounds. Organic chemistry primarily deals with the structure and chemical composition of organic compounds, the physical and chemical properties of organic compounds, and the chemical reactions undergone by these compounds.
Reaction Intermediates in Organic Chemistry:
Intermediates can be understood as the first product of a consecutive reaction. For example, in a chemical reaction, if A→B and B→C, then, B can be said to be the intermediate for reaction A→C. The reactions in organic chemistry occur via the formation of these intermediates.
Reagents in Organic Chemistry:
Reagents are the chemicals that we add to bring about a specific change to an organic molecule. Any general reaction in organic chemistry can be written as:
Substrate + Reagent → Product
Where the substrate is an organic molecule to which we add the reagent. Based on the ability to either donate or abstract electrons, the reagents can be classified as:
- Electrophiles
- Nucleophiles