નીચેનામાંથી શેમાં હેલોફોર્મ પ્રકિયા આવે છે?

$(i)$ $CH_3CH_2COCH_2Cl$ $(ii)$ $C_6H_5COCH_3$

$(iii)$ $C_6H_5COCHCl_2$ $(iv)$ $CH_3CH_2COCCl_3$

Question

નીચેનામાંથી શેમાં હેલોફોર્મ પ્રકિયા આવે છે?

$(i)$ $CH_3CH_2COCH_2Cl$ $(ii)$ $C_6H_5COCH_3$

$(iii)$ $C_6H_5COCHCl_2$ $(iv)$ $CH_3CH_2COCCl_3$

AIIMS 2011, Medium

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Solution

d
If we observe the haloform reaction carefully, we see that $-COCH_3$ group is first halogenated to the trihalo $-COCX_3$ through monohalogeno and dihalogeno compound. It is the $-COCX_3$ part which then undergoes nucleophilic addition. The product easily loses $-CX_3$ since it is a very good leaving group

Thus all compounds $(I\, to \,IV)$ are ultimately converted to $CHCl_3$ (chloroform)

$\mathop {\begin{array}{*{20}{c}}
\,\,\,\,{O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
\,\,\,\,{||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{C{H_3} - C - C{H_3}\xrightarrow{{{X_2},O{H^ - }}}}
\end{array}}\limits_{I\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} $ $\mathop {\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{\,\,\,\,\,\,\,\,\,\,||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{C{H_3} - C - C{H_2}Cl \to }
\end{array}}\limits_{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,II\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} $ $\mathop {\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{\,\,\,\,\,\,\,\,\,\,||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{C{H_3} - C - CHC{l_2} \to }
\end{array}}\limits_{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,III\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} $ $\mathop {\begin{array}{*{20}{c}}
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{\,\,\,\,\,\,\,\,\,\,\,\,\,\,||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} \\
{C{H_3} - C - CC{l_3}\,\,\,\,\,\,\,\,}
\end{array}}\limits_{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,IV\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,} $

$\begin{matrix}
\,\,O\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
\,\,||\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\, \\
C{{H}_{3}}-C-CC{{l}_{3}}\xrightarrow{O{{H}^{-}}} \\
\end{matrix}$ $\begin{matrix}
\begin{matrix}
\,{{O}^{-}} \\
|\,\,\,\, \\
\end{matrix}\,\,\,\, \\
C{{H}_{3}}-C-CC{{l}_{3}}\to \\
|\,\,\,\,\,\,\, \\
OH\,\,\,\,\,\, \\
\end{matrix}$ $\begin{array}{*{20}{c}}
{\,\,\,\,\,\begin{array}{*{20}{c}}
{\,\,\,\,\,O\,\,} \\
{||}
\end{array}\,\,\,\,\,\,\,} \\
{C{H_3} - C - \mathop C\limits^ - C{l_3}} \\
{\,\,\,\,\,|\,\,\,\,\,\,\,\,} \\
{\,\,\,\,\,\,\,\,\,\,OH\,\,\,\,\,\,\,}
\end{array}$

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