1 $\begin{array}{*{20}{c}}
{\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}} \\
{\,\,\,\,\,\,\,\,|}
\end{array}} \\
{C{H_2} = CH - C - COOH} \\
{\,\,\,\,\,\,\,\,\,\,|} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_3}}
\end{array}$ $\xrightarrow{{NaOH\, + \,CaO\,/\,\Delta }}$ $\begin{array}{*{20}{c}}
{C{H_2} = CH - CH - C{H_3}} \\
{\,\,\,\,\,\,\,\,\,\,|} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,C{H_{3\,}}}
\end{array}$
2 $\begin{array}{*{20}{c}}
{\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,COOH} \\
{|\,\,\,\,\,} \\
{H - C - C{H_3}} \\
{|\,\,\,\,\,\,}
\end{array}} \\
{H - C - C{H_3}} \\
{|\,\,\,\,\,\,\,} \\
{D\,\,\,\,\,\,}
\end{array}\,$ $\xrightarrow[{(ii)\,\,B{r_2}/CC{l_4}/\Delta }]{{(i)\,\,A{g_2}O}}$ $\begin{array}{*{20}{c}}
{\begin{array}{*{20}{c}}
{Br} \\
{|\,\,\,\,\,} \\
{H - C - C{H_3}} \\
{|\,\,\,\,\,}
\end{array}} \\
{H - C - C{H_3}} \\
{|\,\,\,\,\,\,} \\
{D\,\,\,\,}
\end{array}$ + Enantiomer
3 $\begin{array}{*{20}{c}}
{C{H_3} - CH - C{H_2} - N{O_2}\xrightarrow[\Delta ]{{O{H^ - }/{H_2}O}}C{H_2} = CH - C{H_2} - N{O_2}} \\
{\,\,\,\,\,\,|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{\,\,F\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}
\end{array}$
4