Question

How is the following conversion carried out?

\[\ce{Methyl magnesium bromide → 2-Methylpropan-2-ol}\]

Answer 1

When methyl magnesium bromide is treated with propane, an adduct is the product which gives 2-methylpropane-2-ol on hydrolysis.

\[\begin{array}{cc}
\ce{H3C}\phantom{..................................}\\
\backslash\phantom{.............................}\\
\ce{C = O + CH3 - MgBr ->}\phantom{.}\\
/\phantom{............................}\\
\ce{H3C}\phantom{..................................}
\end{array}\]\[\begin{bmatrix} 
\ce{CH3}\phantom{..}\\
|\phantom{....}\\
\ce{CH3 - C - \overset{-}{O}\overset{+}{Mg}Br}\\
|\phantom{....}\\
\ce{\underset{Adduct}{CH3}}\phantom{..}\\
\end{bmatrix}\]\[\begin{array}{cc}
\ce{OH}\phantom{......}\\
|\phantom{........}\\
\ce{->[H2O]CH3 - C - CH3 + Mg(OH)Br}\\
|\phantom{........}\\
\ce{\underset{2-Methylpropan-2-ol}{CH3}}\phantom{.....}\\
\end{array}\]