SN1 (solvolysis in ethanol): practice and mechanism
The solvent ethanol is the nucleophile here (solvolysis): it traps the carbocation and an ethyl ether forms.
Example
The tertiary carbocation is trapped by the solvent ethanol (solvolysis). After loss of a proton an ether forms. The alkene from E1 is a side product.
Mechanism step by step
- 1
The halide leaves and the tertiary carbocation forms (slow step).
- 2
An ethanol molecule of the solvent attacks with its oxygen.
- 3
After losing a proton the ether is present; alongside, the alkene forms via E1.
Practice tasks
Which product forms, which reagent is needed? After each answer you see the explanation.
Which main product forms?
Typical mistakes
Often confused with: SN1 (hydrolysis) · E2 (Zaitsev product)
Frequently asked questions
What does solvolysis mean?
The solvent itself is the nucleophile, here ethanol. With water it is called hydrolysis.
Why does an alkene form too?
Instead of taking a nucleophile, the carbocation can lose a proton from the neighbouring carbon (E1). Higher temperature favours this.