A) Octyl-chloride
B) 2-chloro-2-methyl-butane
C) Dimethyl-chloro-octane
D) Isopentyl-chloride
Correct Answer: D
Solution :
\[RCl\]reacts with Na to give 2, 7-dimethyl octane (by Wurtz reaction). \[R-Cl+2Na+ClR\xrightarrow{{}}R-R+2NaCl\] Hence, \[\underset{2,7-dimethyl\text{ }octane}{\mathop{R-R=C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{2}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{3}}}}\,\] Here, \[R=\left( C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,-C{{H}_{2}}-C{{H}_{2}}- \right)\] \[RLi\]reacts with water to form isopentane. \[RLi\xrightarrow[{}]{{{H}_{2}}O}\underset{isopentane}{\mathop{C{{H}_{3}}\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,C{{H}_{2}}C{{H}_{3}}}}\,\] Therefore,\[R\text{ }Cl\]is\[\underset{isopentyl-\text{ }chloride}{\mathop{C{{H}_{3}}\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{CH}}\,C{{H}_{2}}C{{H}_{2}}Cl}}\,\]
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