Question

What happens when acetyl chloride is treated with an excess of CH₃MgI?

Answer 1

\[\begin{array}{cc}
\phantom{..................}\ce{O}\phantom{...........................}\ce{OMgI}\phantom{...............}\ce{OH}\phantom{...........}\ce{I}\phantom{.........}\\
\phantom{............}||\phantom{............................}|\phantom{.....................}|\phantom{...........}/\phantom{....}\\
\ce{\underset{\text{Acetaldehyde}}{CH3 - C - H} + CH3MgI -> CH3 - C - H ->[H2O/H+] CH3 - C - H + Mg}\\
\phantom{........................................}|\phantom{.....................}|\phantom{............}\backslash\phantom{..}\\
\phantom{...............................................}\ce{CH3}\phantom{............}\ce{\underset{\text{Isopropylalcohol (2°)}}{CH3}}\phantom{.....}\ce{OH}\phantom{.........}
\end{array}\]

\[\begin{array}{cc}
\phantom{..................}\ce{O}\phantom{...........................}\ce{OMgI}\phantom{....................}\ce{OH}\phantom{.............}\ce{I}\phantom{...........}\\
\phantom{..................}||\phantom{...............................}|\phantom{.......................}|\phantom{.............}/\phantom{...........}\\
\ce{\underset{\text{Acetone}}{CH3 - C - CH3} + CH3MgI -> CH3 - C - CH3 ->[H2O/H+] CH3 - C - CH3 + Mg}\\
\phantom{.............................................}|\phantom{.......................}|\phantom{..............}\backslash\phantom{.....}\\
\phantom{.................................................}\ce{CH3}\phantom{................}\ce{\underset{\text{Tert - Butylalcohol(3°)}}{CH3}}\phantom{.....}\ce{OH}\phantom{.........}
\end{array}\]