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Question
Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism and why?
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Which alkyl halide from the following pairs would you expect to react more rapidly by an SN2 mechanism and why?
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Solution
SN2 reaction:
- The SN2 reaction is a nucleophilic substitution reaction where a bond is broken and another is formed synchronously.
- Two reacting species are involved in the rate-determining step of the reaction.
- The term 'SN2' stands for – Substitution Nucleophilic Bimolecular.
- The SN2 reaction is favored in carbon that has the least steric hindrance as this includes the attacking of a nucleophile.
The alkyl halide that would react more rapidly by an SN2 mechanism:
- Among the two given compounds; (1-Bromopropane)& (2-Bromobutane),the compound 1-Bromopropane will undergo SN2 reaction more rapidly than the 2-Bromobutane.
- As the steric hindrance is very low at the site of attack of the nucleophile in the case of 1-Bromopropane, hence SN2 reaction more rapidly takes place in this case.
- Here is a reaction to demonstrate the attack of Cyanide ion which is a nucleophile on 1-Bromopropane.
- While there is a steric hindrance at the site of attack of nucleophile in 2-Bromobutane that can be observed in the reaction given below.
- Thus, among 1-Bromopropane and 2-Bromobutane; 1-bromopropane has the least steric hindrance as the bromine atom is attached to the primary carbon location.
- Therefore, (1-Bromopropane) undergoes faster SN2 reaction upon being attacked by a nucleophile.
Hence, the alkyl halide from the given pairs that would you expect to react more rapidly by an SN2 mechanism is (1-Bromopropane).
SN2 reaction:
- The SN2 reaction is a nucleophilic substitution reaction where a bond is broken and another is formed synchronously.
- Two reacting species are involved in the rate-determining step of the reaction.
- The term 'SN2' stands for – Substitution Nucleophilic Bimolecular.
- The SN2 reaction is favored in carbon that has the least steric hindrance as this includes the attacking of a nucleophile.
The alkyl halide that would react more rapidly by an SN2 mechanism:
- Among the two given compounds; (1-Bromopropane)& (2-Bromobutane),the compound 1-Bromopropane will undergo SN2 reaction more rapidly than the 2-Bromobutane.
- As the steric hindrance is very low at the site of attack of the nucleophile in the case of 1-Bromopropane, hence SN2 reaction more rapidly takes place in this case.
- Here is a reaction to demonstrate the attack of Cyanide ion which is a nucleophile on 1-Bromopropane.
- While there is a steric hindrance at the site of attack of nucleophile in 2-Bromobutane that can be observed in the reaction given below.
- Thus, among 1-Bromopropane and 2-Bromobutane; 1-bromopropane has the least steric hindrance as the bromine atom is attached to the primary carbon location.
- Therefore, (1-Bromopropane) undergoes faster SN2 reaction upon being attacked by a nucleophile.
Hence, the alkyl halide from the given pairs that would you expect to react more rapidly by an SN2 mechanism is (1-Bromopropane).
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