Question

An organic compound A with the molecular formula (+) C₄H₉Br undergoes hydrolysis to form (+) C₄H₉OH. Give the structure of A and write the mechanism of the reaction.

Answer 1

\[\begin{array}{cc}\ce{C2H5 - CH - CH3}\\
|\phantom{.}\\\ce{Br}\end{array}\]

Mechanism:

\[\begin{array}{cc}
\ce{H}\phantom{.................}\ce{H}\\
|\phantom{..................}|\\
\ce{H3C - C - C2H5 ->[Slow step] C^⊕ + B\overset{⊖}{r}}\\
\phantom{...}|\phantom{................}/\phantom{...}\backslash\\
\phantom{.......}\ce{Br}\phantom{...........}\ce{H3C}\phantom{....}\ce{C2H5}
\end{array}\]

\[\begin{array}{cc}
\ce{H}\phantom{....................}\ce{H}\phantom{...............}\ce{H}\phantom{.......}\\
|\phantom{.....................}|\phantom{................}|\phantom{.......}\\
\ce{C^⊕ + O\overset{⊖}{H} ->[Fast] H3C - C - OH + HO - C - CH3}\\
/\phantom{..}\backslash\phantom{....................}|\phantom{.................}|\phantom{.........}\\
\ce{H3C}\phantom{...}\ce{C2H5}\phantom{...............}\ce{C2H5}\phantom{.............}\ce{C2H5}\phantom{........}
\end{array}\]