
$C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}Br\xrightarrow{NaCN}$ $X\xrightarrow[heat]{{{H}_{3}}{{O}^{+}}}Y\xrightarrow[{{H}^{+}}]{C{{H}_{3}}C{{H}_{2}}OH}Z$

$\begin{matrix}
O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{F}_{3}}\,C\,OH+C{{H}_{3}}\,CH\,C{{H}_{3}} \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,| \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH \\
\end{matrix}\xrightarrow{{{H}_{2}}S{{O}_{4}}}\begin{matrix}
O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{F}_{3}}\,C\,OCH\,C{{H}_{3}}+{{H}_{2}}O \\
|\,\,\,\,\,\,\,\,\,\,\,\, \,\,\,\, \\
C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\, \\
\end{matrix}$
$\begin{matrix}
O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{H}_{3}}-C-OH+C{{H}_{3}}-OH\overset{cat.}{\longleftrightarrow} \\
\end{matrix}\begin{matrix}
O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{H}_{3}}-C-O-C{{H}_{3}}+{{H}_{2}}O \\
\end{matrix}$