Problem 8. (8 points) Choose between the following options to maximize the probability of an SN2 mechanism and to minimize the probability of an Sn1 mechanism. Briefly explain each of your choices. (For part e E-dielectric constant). a. Reactant LG b. Nucleophile Me3N or c. Solvent: CF CH2OH CH3OH -39) -33) d. Concentration of Nucleophile High Low or Solution SN2 is nucleophilic substitution bimolecular which occur in single step. the SN2 substitution is favoured by the strong nucleophile , better leaving group and aprotic polar solvents 1) CH3-CH(CH3)-LG favours the SN2 reaction. The SN2 is favoured by less hindered reactant, as ph-CH(CH3)-LG is bulky when compared to the CH3-CH(CH3)-LG the later favours the SN2 reaction as less hindered. Where as first one favours the SN1 as it forms a stable carbocation. 2)The SN2 is favoured by the storng nucleohilie whereas the SN1 is independent of the nucleophile. Me3N is strong nucleophile than N3- as there are 3 elelctron donating methyl group to nitrogen in Me3N it act as strong nucleophile when compared to N3- 3) CH3OH favours the SN2 reaction. Polar aprotic solvent with low dielectric constant favours the SN2 reaction.Even though both the given solvent are protic solvents.The CH3OH has lower dielectric constant value than CF3CH2OH. CH3OH is less acidic when compared to CF3CH2OH.The more acidic solvent forms the strong bond with leaving group favouring the SN1 reaction. 4) High concentration of nucleophile is required for SN2 reaction as the SN2 reaction is dependent on the concentration of both the reactants and nucleophile, the increase in concentration of nucleophile increase the rate of reaction .

1. Problem 8. (8 points) Choose between the following options to maximize the probability of an
SN2 mechanism and to minimize the probability of an Sn1 mechanism. Briefly explain each of
your choices. (For part e E-dielectric constant). a. Reactant LG b. Nucleophile Me3N or c.
Solvent: CF CH2OH CH3OH -39) -33) d. Concentration of Nucleophile High Low or
Solution
SN2 is nucleophilic substitution bimolecular which occur in single step. the SN2 substitution is
favoured by the strong nucleophile , better leaving group and aprotic polar solvents
1) CH3-CH(CH3)-LG favours the SN2 reaction.
The SN2 is favoured by less hindered reactant, as ph-CH(CH3)-LG is bulky when compared to
the CH3-CH(CH3)-LG the later favours the SN2 reaction as less hindered. Where as first one
favours the SN1 as it forms a stable carbocation.
2)The SN2 is favoured by the storng nucleohilie whereas the SN1 is independent of the
nucleophile. Me3N is strong nucleophile than N3- as there are 3 elelctron donating methyl group
to nitrogen in Me3N it act as strong nucleophile when compared to N3-
3) CH3OH favours the SN2 reaction. Polar aprotic solvent with low dielectric constant favours
the SN2 reaction.Even though both the given solvent are protic solvents.The CH3OH has lower
dielectric constant value than CF3CH2OH. CH3OH is less acidic when compared to
CF3CH2OH.The more acidic solvent forms the strong bond with leaving group favouring the
SN1 reaction.
4) High concentration of nucleophile is required for SN2 reaction as the SN2 reaction is
dependent on the concentration of both the reactants and nucleophile, the increase in
concentration of nucleophile increase the rate of reaction