$\begin{matrix}
\begin{matrix}
\,\,\,\,\,C{{H}_{3}} \\
| \\
\end{matrix}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{H}_{3}}-C-C{{H}_{2}}C{{H}_{2}}OH \\
|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{H}_{3}}\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
\end{matrix}$ $\xrightarrow[{{H_2}O,heat}]{{{K_2}C{r_2}{O_7};{H_2}S{O_4}}}A$ $\xrightarrow{{SOC{l_2}}}B\xrightarrow[{(2{\kern 1pt} mole)}]{{{{(C{H_3})}_2}NH}}C$ $\xrightarrow[{2.{\kern 1pt} {H_2}O}]{{\begin{array}{*{20}{c}}
{1.{\kern 1pt} LiAl{H_4}} \\
{diethyl{\kern 1pt} {\kern 1pt} ether}
\end{array}}}D$
(Figure) $\xrightarrow[FeB{{r}_{3}}]{B{{r}_{2}}}B\xrightarrow{Sn\,/\,HCl}C$ $\xrightarrow[HCl]{NaN{{O}_{2}}}D\xrightarrow[HBr]{CuBr}E$
