Answer:
The alkane which gives four isomeric
monochloro products is 2,2-dimethylpentane. Since there are four types of
carbon atoms present, there are four isomeric products. The products are given
ahead.
\[\underset{2,2-\text{Dimethylpentane}\,({{C}_{7}}{{H}_{16}})}{\mathop{\overset{1{}^\circ
}{\mathop{C}}\,{{H}_{3}}-\overset{\begin{smallmatrix}
1{}^\circ \\
C{{H}_{3}}
\\
|
\end{smallmatrix}}{\mathop{\underset{\begin{smallmatrix}
| \\
{}^{1{}^\circ }C{{H}_{3}}
\end{smallmatrix}}{\mathop{{}^{4{}^\circ
}C}}\,}}\,-\overset{3{}^\circ }{\mathop{C}}\,{{H}_{2}}-\overset{2{}^\circ
}{\mathop{C}}\,{{H}_{2}}-\,\,\,\,\,\,\,\,\,\overset{1{}^\circ
}{\mathop{C}}\,{{H}_{3}}}}\,\,\xrightarrow[hv]{C{{l}_{2}}}\] \[Cl-\underset{1-\text{Chloro}-2,\,\,2-\text{dimethylpentane}}{\mathop{\overset{1}{\mathop{C}}\,{{H}_{2}}-\overset{\begin{smallmatrix}
\\
C{{H}_{3}}
\\
|
\end{smallmatrix}}{\mathop{\underset{\begin{smallmatrix}
| \\
{}^{{}}C{{H}_{3}}
\end{smallmatrix}}{\mathop{{}^{2}C}}\,}}\,-\overset{3}{\mathop{C}}\,{{H}_{2}}-\overset{4}{\mathop{C}}\,{{H}_{2}}-\,\,\,\,\,\,\,\,\,\overset{5}{\mathop{C}}\,{{H}_{3}}+}}\,\,\]
\[\underset{\text{5-Chloro-2,}\,\text{2}\,\text{dimethylpentane}}{\mathop{\overset{1}{\mathop{C}}\,{{H}_{3}}-\underset{\begin{smallmatrix}
| \\
C{{H}_{3}}
\end{smallmatrix}}{\overset{\begin{smallmatrix}
C{{H}_{3}} \\
|
\end{smallmatrix}}{\mathop{\overset{2}{\mathop{C}}\,}}}\,-\overset{3}{\mathop{C}}\,{{H}_{2}}-\overset{4}{\mathop{C}}\,{{H}_{2}}-\overset{5}{\mathop{C}}\,{{H}_{2}}Cl}}\,+\]\[\underset{\text{4-Chloro-2,}\,\text{2}\,\text{dimethylpentane}}{\mathop{\overset{1}{\mathop{C}}\,{{H}_{3}}-\underset{\begin{smallmatrix}
| \\
C{{H}_{3}}
\end{smallmatrix}}{\overset{\begin{smallmatrix}
C{{H}_{3}} \\
|
\end{smallmatrix}}{\mathop{\overset{2}{\mathop{C}}\,}}}\,-\overset{3}{\mathop{C}}\,{{H}_{2}}-\underset{\begin{smallmatrix}
| \\
Cl
\end{smallmatrix}}{\mathop{\overset{4}{\mathop{C}}\,}}\,H-\overset{5}{\mathop{C}}\,{{H}_{3}}}}\,+\]\[\underset{\text{3-Chloro-2,}\,\text{2}\,\text{dimethylpentane}}{\mathop{\overset{1}{\mathop{C}}\,{{H}_{3}}-\underset{\begin{smallmatrix}
| \\
C{{H}_{3}}
\end{smallmatrix}}{\overset{\begin{smallmatrix}
C{{H}_{3}} \\
|
\end{smallmatrix}}{\mathop{\overset{2}{\mathop{C}}\,}}}\,-\underset{\begin{smallmatrix}
| \\
Cl
\end{smallmatrix}}{\mathop{\overset{3}{\mathop{C}}\,}}\,H-\overset{4}{\mathop{C}}\,{{H}_{2}}}}\,-\overset{5}{\mathop{C}}\,{{H}_{3}}\]
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