It is $\alpha $ - subtitution when a carboxylic acid having $\alpha $ - hydrogens is treated with chlorine or bromine in presence of small amount of red phosphorous.
$R-C{{H}_{2}}COOH\,+\,{{X}_{2}}\,\xrightarrow{P}$ $\begin{matrix}
X\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
|\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
RCH-COOH+HX \\
\end{matrix}$ $(X\,=\,Cl,\,Br)$
$(A)\,{{C}_{8}}{{H}_{10}}\xrightarrow{KMn{{O}_{4}}}(B){{C}_{8}}{{H}_{6}}{{O}_{4}}\xrightarrow[Fe]{B{{r}_{2}}}{{C}_{8}}{{H}_{5}}Br{{O}_{4}}(C)$ (માત્ર એક જ નીપજ )
$Hex - 3 - ynal\xrightarrow[\begin{subarray}{l}
(ii)\,PB{r_3} \\
(i)\,Mg/ether \\
(i)\,C{O_2}/{H_3}{O^ + }
\end{subarray} ]{{(i)\,NaB{H_4}}}\,?$