$(1)$ $CH_3CH_2-CH_2-OH$
$(2)$ $\begin{array}{*{20}{c}}
{C{H_3} - C{H_2} - CH - OH} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}}
\end{array}$
$(3)$ $\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,C{H_3}} \\
\,\,\,\,\,\,|
\end{array}} \\
{C{H_3} - C{H_2} - C - OH} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}}
\end{array}$
$\begin{matrix}
\begin{matrix}
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\,C{{H}_{3}} \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\,| \\
\end{matrix} \\
C{{H}_{3}}-C{{H}_{2}}-{{C}^{\oplus }} \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\ \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\,| \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\, \,\,\,\,C{{H}_{3}} \\
\end{matrix}$ $>$ $\begin{array}{*{20}{c}}
{C{H_3} - C{H_2} - CH - O{H^ \oplus }} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}}
\end{array}$ $>$ $C{H_3} - C{H_2} - C{H_2} - O{H^ \oplus }$

$I.$ $DDT$ $II.$ Gammerane
$III.$ Carbon tetrachloride $IV.$ Chlorobenzene

${H_2}C = CHC{H_2}Br\xrightarrow{{NaCN}}Y\xrightarrow[{2.\,{H_3}{O^ + }}]{\begin{subarray}{l}
1.{C_6}{H_5}MgBr\, \\
diethylether
\end{subarray} }Z$
$(I)$ Benzylchloride
$(II)$ $p-$ Methoxy benzyl chloride
$(III)$ $p-$ Nitro benzyl chloride