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Question
Write the reactions of Williamson synthesis of 2-ethoxy-3-methylpentane starting from ethanol and 3-methylpentan-2-ol.
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Solution
\[\begin{array}{cc}
\phantom{}\ce{CH3 - CH2 - CH - CH - OH ->[Na] CH3 - CH2 - CH - CH - ONa}\phantom{}\\
\phantom{........................}|\phantom{.........}|\phantom{............................................}|\phantom{.........}|\phantom{...............}\\
\phantom{................}\ce{CH3}\phantom{....}\ce{CH3}\phantom{.....................................}\ce{CH3}\phantom{....}\ce{CH3}\phantom{...}\\
\end{array}\]
\[\ce{C2H5OH ->[HBr] C2H5Br}\]
\[\begin{array}{cc}
\phantom{}\ce{CH3 - CH2 - CH - CH - ONa + C2H5Br}\phantom{}\\
\phantom{.}|\phantom{.........}|\phantom{..........}\\
\phantom{..}\ce{CH3}\phantom{....}\ce{CH3}\phantom{.......}\\
\phantom{}\ce{\downarrow}\phantom{.....}\\
\phantom{}\ce{CH3 - CH2 - CH - CH - OC2H5}\phantom{......}\\
\phantom{.........}|\phantom{.........}|\phantom{..........}\\
\phantom{..........}\underset{\text{2-Ethoxy-3-methylpentane}}{\ce{CH3}\phantom{....}\ce{CH3}}\phantom{.......}
\end{array}\]
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