$\,\text{C}{{\text{H}}_{\text{3}}}\text{Br }\xrightarrow{\text{KCN}}A\xrightarrow{{{H}_{3}}O}B\xrightarrow{LiAl{{H}_{4}}}C$
${H_2}C = CHC{H_2}Br\xrightarrow{{NaCN}}Y\xrightarrow[{2.\,{H_3}{O^ + }}]{\begin{subarray}{l}
1.{C_6}{H_5}MgBr\, \\
diethylether
\end{subarray} }Z$
$(1)$ $CH_3CH_2-CH_2-OH$
$(2)$ $\begin{array}{*{20}{c}}
{C{H_3} - C{H_2} - CH - OH} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}}
\end{array}$
$(3)$ $\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,C{H_3}} \\
\,\,\,\,\,\,|
\end{array}} \\
{C{H_3} - C{H_2} - C - OH} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}}
\end{array}$