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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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\[\begin{array}{cc}\ce{CH3 - CH = CH3 ->[Red P/Br2] A ->[Ag2O/H2O]B}\\|\phantom{.........................}\\
\ce{OH\phantom{.......................}}\end{array}\]
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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}\\
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\ce{CH3}\phantom{...............}\\
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