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Question
The following will react faster by SN1 mechanism
Options
1-chloropropane
2-chloropropane
2-chloro-2-methylpropane
chloroethane
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Solution
2-chloro-2-methylpropane
Explanation:
Reactivity order of alkyl halides towards SN1 mechanism: 3° > 2° > 1° > CH3X
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\[\begin{array}{cc}
\ce{CH3}\phantom{.......}\\
|\phantom{.........}\\
\ce{CH3 - c - CH2 - Cl ->[Na/dry ether]}\\
|\phantom{.........}\\
\ce{CH3}\phantom{.......}
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\[\begin{array}{cc}
\ce{CH3}\phantom{................}\\
|\phantom{...................}\\
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|\phantom{...................}\\
\ce{CH3}\phantom{................}
\end{array}\]
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\[\begin{array}{cc}
\ce{CH3}\phantom{................}\\
|\phantom{..................}\\
\ce{CH3 - C - CH2 - Cl ->[Na/dry ether]A}\\
|\phantom{..................}\\
\ce{CH3}\phantom{................}
\end{array}\]
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\[\begin{array}{cc}
\ce{CH3}\phantom{.................}\\
|\phantom{...................}\\
\ce{CH3 - C - CH2 - Cl ->[Na/dry ether] A}\\
|\phantom{...................}\\
\ce{CH3}\phantom{.................}
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