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Question
In the following pair of halogen compounds, which compound undergoes a faster SN1 reaction?
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Solution
The activity of halogen compounds in SN1 reaction depends on the stability of the carbocation formed due to ionization. The order of stability is tertiary > secondary > primary. Hence, 2° alkyl chloride is more active than 1° alkyl chloride. Hence, 2° alkyl chloride is more active in SN1 reaction.
The halogen which reacts faster due to the greater stability of the 2° carbocation than the 1° carbocation is:
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\phantom{}\ce{\underset{}{(CH3)2CH - CH2Br} ->[C2H5OH] \underset{}{(CH3)2CH - CH2OC2H5 + HBr}}\\
\end{array}\]
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