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The Sn1 reaction results in similar products as the Sn2 reaction, but the
mechanism is entirely unique. It involves both a substrate, such as
t-butyl bromide, and a nucleophile. T-butyl bromide, while being a
terrible substrate for the Sn2 reaction reacts well in the Sn1 reaction
With the Sn1 reaction, t-butyl bromide reacts quite quickly with a
nucleophile to form the substitution product.
In the Sn1
reaction, the concentration of the substrate effects the reaction rate,
but changing the concentration of the nucleophile has no effect on the
rate. The Sn1 reaction follows the following rate equation:
Rate = kr[substrate].
This means
that only the substrate is involved in the rate determining step.
The Rate
Determining Step--Formation of the carbocation:

Followed by attack of the nucleophile on the carbocation:

Last, the removal of a proton by the bromine:

Since the nucleophile is not involved in the rate determining step, the
concentration or the nucleophilicity of the nucleophile has no
effect on the reaction rate. This means that poor nucleophiles
such as water and alcohols can react to form alcohols and ethers. |