$Hex - 3 - ynal\xrightarrow[\begin{subarray}{l}
(ii)\,PB{r_3} \\
(i)\,Mg/ether \\
(i)\,C{O_2}/{H_3}{O^ + }
\end{subarray} ]{{(i)\,NaB{H_4}}}\,?$
$\begin{matrix}
O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{F}_{3}}\,C\,OH+C{{H}_{3}}\,CH\,C{{H}_{3}} \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,| \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,OH \\
\end{matrix}\xrightarrow{{{H}_{2}}S{{O}_{4}}}\begin{matrix}
O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{F}_{3}}\,C\,OCH\,C{{H}_{3}}+{{H}_{2}}O \\
|\,\,\,\,\,\,\,\,\,\,\,\, \,\,\,\, \\
C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\, \\
\end{matrix}$
$C{H_3}COON{H_4}\xrightarrow{\Delta }X\,\xrightarrow{{{P_2}{O_5}}}\,Y\,\xrightarrow{{{H_2}O/{H^ + }}}\,Z$