- A$2 -$ chloropropanal
- B$2 -$ chlorobutane
- C$2 -$ chloropentane
- ✓$2 -$ chloro $- 2-$ methylbutane
$\underset{2-chloropropanol}{\mathop{\begin{matrix}
\,Cl\, \\
|\,\, \\
C{{H}_{3}}-C-CHO \\
|\,\, \\
H\, \\
\end{matrix}}}\,$ $\underset{2-chlorobu\tan e\,(chiral)}{\mathop{\begin{matrix}
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,Cl \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,|\,\,\,\,\,\, \\
C{{H}_{3}}-C{{H}_{2}}-C-C{{H}_{3}} \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,| \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,H \\
\end{matrix}}}\,$
$\underset{(chiral)}{\mathop{\underset{2-chloropen\tan e}{\mathop{\begin{matrix}
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,Cl \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,| \\
C{{H}_{3}}-C{{H}_{2}}-C{{H}_{2}}-C-C{{H}_{3}} \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,| \\
\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,H \\
\end{matrix}}}\,}}\,$ $\underset{(achiral)}{\mathop{\underset{2-chloro-2-methylbu\tan e}{\mathop{\begin{matrix}
C{{H}_{3}} \\
| \\
C{{H}_{2}}-C-C{{H}_{3}} \\
| \\
Cl \\
\end{matrix}}}\,}}\,$
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(figure) $\xrightarrow[CC{{l}_{4}}]{B{{r}_{2}}}(A)\xrightarrow[(ii)\,NaN{{H}_{2}}]{(i)\,alc.\,KOH}(B)\xrightarrow[(ii)\,C{{H}_{3}}-Cl]{(i)\,NaN{{H}_{2}}}(C)$
${H_3}C - C \equiv CH\,\xrightarrow[{HgS{O_4}}]{{{H_2}O,\,{H_2}S{O_4}}}\,\mathop {Intermediate}\limits_{(A)} \,$$ \to \,\mathop {\Pr oduct}\limits_{(B)} $
