c
$\begin{matrix}
{{H}_{2}}C=CH-C{{H}_{2}}-C{{H}_{2}}-CH-C{{H}_{3}}\xrightarrow[Pyridine]{SOC{{l}_{2}}} \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,| \,\,\,\,\,\,\,\, \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH\,\,\,\,\,\, \\
\end{matrix}$ $\begin{matrix}
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,Cl \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\, \\
{{H}_{2}}C=CH-C{{H}_{2}}-C{{H}_{2}}-CH-C{{H}_{3}} \\
\end{matrix}$ $\xrightarrow{{{O_3}\,/\,Zn\,\,({H_2}O)}}$ $\begin{array}{*{20}{c}}
{O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,Cl\,\,\,\,\,\,\,\,} \\
{||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,} \\
{H - C - C{H_2} - C{H_2} - CH - C{H_3}}
\end{array}$ $\xrightarrow{{NaB{H_4}}}$ $\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,Cl} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\
{HO - C{H_2} - C{H_2} - C{H_2} - CH - C{H_3}}
\end{array}$