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

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The SN1 mechanism requires a carbocation intermediate, which is unstable in the case of alkenes due to the lack of a positive charge stabilization.
Updated On: Mar 17, 2025
  • \(\text{C}_6\text{H}_5\text{CH}_2\text{Cl}\)
  • \(\text{CH}_2\text{CH} - \text{CH}_2\text{Cl}\)
  • \((\text{CH}_3)_3 \text{C} - \text{Cl}\)
  • \(\text{CH}_3 - \text{CH} = \text{CH} - \text{Cl}\) 

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The Correct Option is D

Solution and Explanation

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. 

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