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Question
Which of the compounds will react faster in SN1 reaction with the –OH ion?
\[\ce{CH3-CH2-Cl}\] or \[\ce{C6H5-CH2-Cl}\]
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Solution
\[\ce{C6H5-CH2-Cl}\]
SN1 reaction proceeds through the formation of carbonation intermediate.
\[\ce{C6H5CH2Cl}\] readily undergoes ionization to give \[\ce{C6H5CH^{+}2}\] carbocation, which is stabilized by resonance.
On the other hand, \[\ce{CH3CH2Cl}\] does not undergo ionization to give \[\ce{CH3CH^{+}2}\] carbonation. Therefore, \[\ce{C6H5CH2Cl}\] reacts faster than \[\ce{CH3CH2Cl}\] with \[\ce{OH-}\] ion.
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