Haloalkanes - What Determines Whether SN1 or SN2 Predominates?

7 important questions on Haloalkanes - What Determines Whether SN1 or SN2 Predominates?

What are the parameters that have an effect on whether a SN1 or a SN2 reaction occurs?

1. The structure of the nucleophile
2. The structure of the haloalkane
3,  The structure of the leaving group
4. The solvent

By what factors are the two nucleophilic substitution reactions mainly governed?

- SN1 reactions are mainly governed by electronic factors, the relative stability of the carbocation.
- SN2 reactions are mainly governed by steric factors

What is the effect of the structure of the haloalkane on the rate of reaction of SN1 reactions?

The SN1 reactions are mainly governed by electronic factors, the stability of the carbocation.
The more substituted a carbocation is the more easily it is formed.
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What is the effect of the structure of the haloalkane on the rate of reaction of SN2 reactions?

The SN2 reactions are mainly governed by steric factors, or steric hinderance. The more easily the nucleophile can access the haloalkane the better the reaction will go.

Why do the halogens Cl- Br- and I- make a good leaving group?

Due to their size and electronegativity form these groups stable anions and are good leaving groups.

What is an aprotic solvent?

An aprotic solvent do not contain an -OH group and therefor cannot serve as a hydrogen bond donor.

What is the effect of the solvent on the type of reaction carried out?

In a protic environment both a cation and an anion can be solvated and are therefor a good environment for carbocation formation and SN1 reactions.
In an aprotic environment only the cation is solvated, making the anion very unstable and reactive.

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