What conditions are present to determine whether a reaction will be sn1 or sn2?
1 Answer
The four main conditions to determine which mechanism, out of a
- the type of carbocation that would be formed (via
#"S"_N1# ) - the extent of steric hindrance
- the strength of the attacking nucleophile
- the type of solvent used
Explanation:
In this explanation, I shall cite the nucleophilic substitution of the molecule with molecular formula
Also remember that nucleophilic substitution reactions are in competition with elimination reactions, but the sets of conditions to favour each of these two reaction types are different to those that cause one type of nucleophilic substitution to be favoured.
1) The Resulting Carbocation
The most important thing to point out is that primary alkyl halides (also known as haloalkanes or halogenoalkanes , since that is the example being used) always undergo
Then first, let us consider the different types of alkyl halides we have at our disposal:
Where R represents an alkyl group (
When an alkyl halide undergoes an
There is then increasing stability of carbocations, with secondary carbocations being more stable than primary ones (and so they are able to form) and tertiary carbocations being the most stable of all.
Therefore secondary and tertiary alkyl halides are capable of undergoing
2) The Extent of Steric Hindrance
This isn't too complicated: steric hindrance is basically the amount of space the entire molecule takes up, and is related to accessibility by complexity of the molecule.
Tertiary alkyl halides have a lot of steric hindrance, since they have three alkyl groups and so lots of hydrogen atoms - this makes it very difficult for a nucleophile to attack as the halogen group leaves (
Steric hindrance decreases in 'simpler' alkyl halides: both primary and secondary alkyl halides are capable of undergoing an
3) Nucleophilic Strength
These final two factors apply only to secondary alkyl halides: the other two types are restricted to only one mechanism, but these may undergo either and will do so in a reaction mixture. These factors only affect which mechanism will occur more frequently.
Strong nucleophiles will attack an electrophilic carbon atom very aggressively; therefore, a strong nucleophile will favour an
As nucleophilic strength decreases (e.g. through increase in charge),
4) Solvent Type
There are two relevant types of solvents: polar protic solvents (EX: water,
Therefore, polar protic solvents exhibit hydrogen bonding: this also allows them to form hydrogen bonds with nucleophiles dissolved in them, which impedes the reactivity of said nucleophiles.
(However polar protics are not all bad, as they really help the original alkyl halide to dissociate, since both are polar.)
Polar protic solvents will favour an
Polar aprotic solvents are used to favour