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Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction
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Minhsan Nguyen
Comparing reactivity of 1-chloroethane and 1-chloropropane in an SN1 reaction
Consider the following assumptions to somehow force these substrates to proceed for $\ce{S_N1}$ reaction mechanism:
Low temperature
Polar protic solvent
Low concentration of nucleophile w.r.t. reactant
Now, in an $\ce{S_N1}$ reaction, the formation of carbocation is must.
The primary factor that determines the reactivity of organic substrates in an $\ce{S_N1}$
reaction is the relative stability of the carbocation that is formed.$\ce{^1}$
According to your linked question: 1-propyl cation would likely be more stable than the ethyl cation.
Hence, your deduction that "the rate of reactivity towards $\ce{S_N1}$ will be greater for the second compound, i.e. $\ce{C3H7Cl}$" is correct.
P.S.: The 1-propyl cation can rearrange itself to a more stable 2$\pu{^o}$ carbocation, but that is not part of RDS to decide the reactivity order.
Consider the following assumptions to somehow force these substrates to proceed for $\ce{S_N1}$ reaction mechanism:
Low temperature
Polar protic solvent
Low concentration of nucleophile w.r.t. reactant
Now, in an $\ce{S_N1}$ reaction, the formation of carbocation is must.
The primary factor that determines the reactivity of organic substrates in an $\ce{S_N1}$reaction is the relative stability of the carbocation that is formed.$\ce{^1}$
According to your linked question: 1-propyl cation would likely be more stable than the ethyl cation.
Hence, your deduction that "the rate of reactivity towards $\ce{S_N1}$ will be greater for the second compound, i.e. $\ce{C3H7Cl}$" is correct.
P.S.: The 1-propyl cation can rearrange itself to a more stable 2$\pu{^o}$ carbocation, but that is not part of RDS to decide the reactivity order.
You avoided all of my question and bounty description. I specifically asked about checking the 4. th step, and also, the second answer on that link contradicts your claim thermodynamically. How did you check the relative stability, that is the question.More
Consider the following assumptions to somehow force these substrates to proceed for $\ce{S_N1}$ reaction mechanism:
Low temperature
Polar protic solvent
Low concentration of nucleophile w.r.t. reactant
Now, in an $\ce{S_N1}$ reaction, the formation of carbocation is must.
The primary factor that determines the reactivity of organic substrates in an $\ce{S_N1}$ reaction is the relative stability of the carbocation that is formed.$\ce{^1}$
According to your linked question: 1-propyl cation would likely be more stable than the ethyl cation.
Hence, your deduction that "the rate of reactivity towards $\ce{S_N1}$ will be greater for the second compound, i.e. $\ce{C3H7Cl}$" is correct.
P.S.: The 1-propyl cation can rearrange itself to a more stable 2$\pu{^o}$ carbocation, but that is not part of RDS to decide the reactivity order.
Reference
Consider the following assumptions to somehow force these substrates to proceed for $\ce{S_N1}$ reaction mechanism:
Low temperature
Polar protic solvent
Low concentration of nucleophile w.r.t. reactant
Now, in an $\ce{S_N1}$ reaction, the formation of carbocation is must.
The primary factor that determines the reactivity of organic substrates in an $\ce{S_N1}$reaction is the relative stability of the carbocation that is formed.$\ce{^1}$
According to your linked question: 1-propyl cation would likely be more stable than the ethyl cation.
Hence, your deduction that "the rate of reactivity towards $\ce{S_N1}$ will be greater for the second compound, i.e. $\ce{C3H7Cl}$" is correct.
P.S.: The 1-propyl cation can rearrange itself to a more stable 2$\pu{^o}$ carbocation, but that is not part of RDS to decide the reactivity order.
Reference
More
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