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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
\[\begin{array}{cc}
\ce{CH3 - CH2 - CH - CH - CH3 ->[Na] CH3 - CH2 - CH - CH - ONa}\\
\phantom{......}|\phantom{......}|\phantom{............................}|\phantom{......}|\phantom{.}\\
\phantom{.........}\ce{\underset{3-Methylpentan-2-ol}{CH3\phantom{...}OH\phantom{}}}\phantom{....................}\ce{\underset{2,3-Dimethylpentane}{\phantom{.}CH3\phantom{..}CH3}}\phantom{..}
\end{array}\]
\[\ce{\underset{Ethanol}{C2H5OH} ->[HBr] \underset{Bromoethane}{C2H5Br}}\]
\[\begin{array}{cc}
\ce{CH3 - CH2 - CH - CH - ONa + C2H5Br -> CH3 - CH2 - CH - CH - OC2H5}\\
\phantom{.......}|\phantom{......}|\phantom{.............................................}|\phantom{......}|\phantom{...........}\\
\phantom{........}\ce{CH3\phantom{...}CH3\phantom{.....................................}}\phantom{}\ce{\underset{2-Ethoxy-3-methylpentane}{\phantom{}CH3\phantom{...}CH3}\phantom{.....}}
\end{array}\]
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