The relative reactivity order of following halides towards \(S_N1\) reaction is: (I) 2-Chloro-2-methylpropane (II) Chloroethane (III) Chlorormethane (IV) Chlorodiphenylmethane |
IV > I > II > III II > III > IV > I I > IV > II > III III > II > I > IV |
IV > I > II > III |
The correct answer is option 1. IV > I > II > III. Let us explain why the correct reactivity order of the halides towards an \(S_N1\) reaction is IV > I > II > III in detail. Understanding \(S_N1\) Reactions: The \(S_N1\) (substitution nucleophilic unimolecular) reaction involves two key steps: Formation of a carbocation: The halide ion leaves, forming a carbocation intermediate. Nucleophilic attack: The nucleophile then attacks the carbocation to form the product. The rate of an \(S_N1\) reaction is determined by the stability of the carbocation intermediate. The more stable the carbocation, the more reactive the halide is in the \(S_N1\) reaction. Analysis of Each Halide: IV. Chlorodiphenylmethane: Carbocation Formed: Benzylic carbocation (a carbocation adjacent to a phenyl group). Stability: The benzylic carbocation is highly stabilized by resonance with the phenyl rings. The resonance delocalizes the positive charge over the aromatic system, making this carbocation very stable. Reactivity: Due to this high stability, chlorodiphenylmethane is extremely reactive in \(S_N1\) reactions. Hence, it ranks as the most reactive. I. 2-Chloro-2-methylpropane: Carbocation Formed: Tertiary carbocation. Stability: The tertiary carbocation is stabilized by hyperconjugation and inductive effects from three alkyl groups, making it quite stable, but not as stable as the benzylic carbocation. Reactivity: The stability of the tertiary carbocation makes 2-chloro-2-methylpropane very reactive in \(S_N1\) reactions, but it is less reactive than chlorodiphenylmethane. II. Chloroethane: Carbocation Formed: Primary carbocation (ethyl carbocation). Stability: The primary carbocation is less stable compared to tertiary and benzylic carbocations due to the absence of significant alkyl group stabilization. Reactivity: Since primary carbocations are less stable, chloroethane is less reactive in \(S_N1\) reactions compared to the tertiary and benzylic systems. III. Chloromethane: Carbocation Formed: Methyl carbocation. Stability: The methyl carbocation is the least stable because it has no alkyl groups to stabilize the positive charge and is very reactive. Reactivity: Due to its extreme instability, chloromethane is the least reactive in \(S_N1\) reactions. Conclusion: The reactivity order based on the stability of the carbocation intermediates is: Chlorodiphenylmethane (IV): Most stable carbocation due to resonance stabilization. 2-Chloro-2-methylpropane (I): Stable tertiary carbocation, but less so compared to benzylic. Chloroethane (II): Less stable primary carbocation. Chloromethane (III): Least stable methyl carbocation. |