$\underset{1}{\mathop{\begin{matrix}
O\,\,\,\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{H}_{3}}COCHC{{H}_{3}} \\
\end{matrix}}}\,$ $\underset{2}{\mathop{\begin{matrix}
\,\,\,\,O \\
\,\,\,\,|| \\
C{{H}_{3}}CCl \\
\end{matrix}}}\,$ $\underset{3}{\mathop{\begin{matrix}
O\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\, \\
C{{H}_{3}}CNHC{{H}_{3}} \\
\end{matrix}}}\,$
$C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}Br\xrightarrow{NaCN}$ $X\xrightarrow[heat]{{{H}_{3}}{{O}^{+}}}Y\xrightarrow[{{H}^{+}}]{C{{H}_{3}}C{{H}_{2}}OH}Z$