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Question
Suggest a suitable reagent to prepare secondary alcohol with the identical group using a Grignard reagent.
Solution
Acetaldehyde reacts with Grignard reagent to give an addition product, which further undergoes acid hydrolysis to yield secondary alcohol, that is isopropyl alcohol.
\[\begin{array}{cc}
\phantom{..}\ce{O}\phantom{........................................}\ce{OMgBr}\phantom{................................}\\
\phantom{.}||\phantom{.........................................}|\phantom{.....................................}\\
\ce{\underset{(Acetaldehyde)}{CH3 - C - H} + \underset{(Methyl magnesium bromide)}{CH3 - Mg - Br} -> CH3 - C - H ->[H^+/H2O] CH3 - CH - OH + MgBr(OH)}\\
\phantom{............................}|\phantom{.....................}|\phantom{.}\\
\phantom{...................................}\ce{CH3}\phantom{.............}\ce{\underset{(isopropyl alcohol)}{CH3}}\phantom{}
\end{array}\]
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\[\begin{array}{cc}
\ce{CH3}\phantom{......}\\
|\phantom{........}\\
\ce{H3C - CH - CH - CH - CH2 - OH}\\
|\phantom{............}|\phantom{........}\\
\ce{Cl}\phantom{...........}\ce{CH3}\phantom{......}
\end{array}\]
