1 $\begin{array}{*{20}{c}}
{Br\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{H - C - C{H_2}COOH} \\
{|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{Br\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,}
\end{array}$
2 \(CH_2(Br) - CH_2 - COBr\)
3 $\begin{array}{*{20}{c}}
{Br\,\,} \\
{|\,\,\,\,\,} \\
{C{H_3} - C - COOH} \\
{|\,\,\,\,\,\,} \\
{Br\,\,\,}
\end{array}$
4 \(CH_2(Br) - CH(Br) - COOH\)
Explanation:
Carbonylic acids reacts with \(C l_{2}\) or \(B r_{2}\) in presence of red \(P\) to give exclusively \(\alpha\) -chloro or \(\alpha\) -bromo acids.
This reaction is called Hell-Volhard-Zelinsky \((HVZ)\) reduction. This reaction is example of \(\alpha -H-\)substitution.
\(C{{H}_{3}}C{{H}_{2}}COOH\,\xrightarrow[-\,HBr]{B{{r}_{2}}/P}\) $\begin{matrix}
\begin{matrix}
Br \\
| \\
\end{matrix}\,\,\,\,\,\, \\
C{{H}_{3}}-C-COOH \\
|\,\,\,\,\,\,\, \\
Br\,\,\,\, \\
\end{matrix}$