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Question
Complete the following reaction.
\[\begin{array}{cc}
\ce{CH3 - CH2 - CH2 - C - CH3 ->[HO - CH2 - CH2 - CH2 - OH][dry HCl] ?}\\
||\phantom{.........}\\
\ce{O}\phantom{.........}
\end{array}\]
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Solution

Overall reaction:
\[\begin{array}{cc}
\ce{CH3 - CH2 - CH2 - C - CH3 ->[H^+][HO - CH2 - CH2 - OH] CH3 - CH2 - CH2 - C - CH3}\phantom{.}\\
\phantom{..................}||\phantom{..........................................}/\phantom{.....}\backslash\phantom{..}\\
\phantom{.............}\ce{\underset{(2-Pentanone)}{O}}\phantom{....................................}\ce{O}\phantom{......}\ce{O}\phantom{}\\
\phantom{............................................................}|\phantom{.......}|\phantom{..}\\
\phantom{.............................................................}\ce{\underset{(2-Pentanone ethylene ketol)}{CH2 - CH2}}
\end{array}\]
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\[\begin{array}{cc} \phantom{...}\ce{R}\phantom{.................}\ce{R}\phantom{..}\ce{H}\phantom{................}\\ \phantom{...}\backslash\phantom{..................}\backslash/\phantom{..........}\phantom{.......}\\ \ce{C = O ->[H2NNH2][KOH/glycol] C + N2 + H2O}\\ \phantom{}/\phantom{............}\phantom{.......}/\phantom{}\backslash\phantom{...............}\\ \phantom{}\ce{R}\phantom{..................}\ce{R}\phantom{..}\ce{H}\phantom{...............} \end{array}\]
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