Isopropyl chloride (2-chloropropane) undergoes hydrolysis mainly by the SN1 (unimolecular nucleophilic substitution) mechanism under suitable conditions.
Explanation:
- Isopropyl chloride is a secondary alkyl halide.
- In polar protic solvents like water or alcohol, it tends to form a relatively stable secondary carbocation, favoring the SN1 mechanism.
SN1 Mechanism Steps:
- Formation of Carbocation (Slow Step):
The C–Cl bond breaks to form a secondary carbocation:
(CH₃)₂CHCl → (CH₃)₂CH⁺ + Cl⁻
- Nucleophilic Attack (Fast Step):
Water (acting as a nucleophile) attacks the carbocation:
(CH₃)₂CH⁺ + H₂O → (CH₃)₂CHOH₂⁺
- Deprotonation:
The intermediate loses a proton to form alcohol:
(CH₃)₂CHOH₂⁺ → (CH₃)₂CHOH + H⁺
Final Product:
Isopropyl alcohol (propan-2-ol)
Important Notes:
- SN1 is favored in polar protic solvents
- Reaction rate depends only on the concentration of the substrate
- Carbocation stability plays a key role
Conclusion:
Isopropyl chloride typically undergoes hydrolysis via the SN1 mechanism, forming isopropyl alcohol as the final product.