Question

The organic halide, which does not undergo hydrolysis by SN1 mechanism is:

Option 1: C₆H₅CH₂Cl

Option 2: CH₂CH - CH₂Cl

Option 3: (CH₃)₃C - Cl

Option 4: CH₃ - CH = CH - Cl

• A. \(\text{C}_6\text{H}_5\text{CH}_2\text{Cl}\)
• B. \(\text{CH}_2\text{CH} - \text{CH}_2\text{Cl}\)
• C. \((\text{CH}_3)_3 \text{C} - \text{Cl}\)
• D. \(\text{CH}_3 - \text{CH} = \text{CH} - \text{Cl}\)

Hint:

The SN1 mechanism requires a carbocation intermediate, which is unstable in the case of alkenes due to the lack of a positive charge stabilization.

Answer 1

The Correct Option is D

The organic halide \(\text{CH}_3 - \text{CH} = \text{CH} - \text{Cl}\) (an alkene) does not undergo hydrolysis by the SN1 mechanism. The SN1 mechanism requires the formation of a stable carbocation intermediate, which is not possible with an alkene. The other compounds, such as \(\text{C}_6\text{H}_5\text{CH}_2\text{Cl}\), undergo hydrolysis via the SN1 mechanism.