Question

How is the following conversion carried out?

\[\ce{Ethyl magnesium chloride -> Propan-1-ol}\]

Answer 1

When ethyl magnesium chloride is treated with methanal, an adduct produces propan-1-ol on hydrolysis.

\[\begin{array}{cc}
\ce{H}\phantom{.................................}\\
\backslash\phantom{..............................}\\
\ce{C = O + C2H5 - MgCl ->}\phantom{.}\\
/\phantom{..............................}\\
\ce{H}\phantom{.................................}
\end{array}\]\[\begin{bmatrix} 
\ce{CH2 - \overset{-}{O}\overset{+}{M}gCl}\\
|\phantom{.............}\\
\ce{C2H5}\phantom{.........}\\
\ce{Adduct}
\end{bmatrix}\]\[\begin{array}{cc}
\ce{->[H2O]}
\ce{\underset{Propan-1-ol}{C3H7 - OH} + Mg(OH)Cl}
\end{array}\]

Answer 2

\[\begin{array}{cc}
\ce{O}\phantom{..........................................................................}\\
||\phantom{..........................................................................}\\
\ce{\underset{chloride}{\underset{Ethyl magnesium}{H3C - CH2 - MgCl}} + C ->[Dry ether] H3C - CH2 - CH2 - OMgCl ->[H3O+] \underset{Propanol}{CH3 - CH2 - CH2 - OH}\\
/\phantom{.}\backslash}\phantom{..........................................................................}\\
\ce{\underset{Formaldehyde}{\ce{H}\phantom{....}\ce{H}}}\phantom{..........................................................................}\\
\end{array}\]