A) \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{3}}\]
B) \[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,H-C{{H}_{2}}-C{{H}_{3}}\]
C) \[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-CH\]
D) \[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{3}}\]
Correct Answer: D
Solution :
Chlorination of\[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{3}}\] \[C{{H}_{3}}-C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{3}}\xrightarrow{C{{l}_{2}}/hw}\]\[C{{H}_{2}}-Cl{{(C{{H}_{2}})}_{3}}C{{H}_{3}}+\] \[C{{H}_{3}}-\overset{\begin{smallmatrix} Cl \\ | \end{smallmatrix}}{\mathop{C}}\,H-{{(C{{H}_{2}})}_{3}}-C{{H}_{3}}+C{{H}_{3}}-C{{H}_{2}}-\]\[\underset{\begin{smallmatrix} | \\ Cl \end{smallmatrix}}{\mathop{C}}\,H-C{{H}_{2}}-C{{H}_{3}}\] Chlorination of \[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,H-C{{H}_{2}}-C{{H}_{3}}\xrightarrow{{}}\]\[C{{H}_{3}}-CH-C{{H}_{2}}-C{{H}_{3}}\xrightarrow[\Delta ]{C{{l}_{2}}/hv}\] \[ClC{{H}_{2}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,H-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{3}}+\]\[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} Cl \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{2}}-C{{H}_{3}}\]\[+C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,H-C{{H}_{2}}-C{{H}_{2}}Cl\] (iii) Chlorination of\[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-H\xrightarrow{{}}C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-H\xrightarrow[\Delta ]{C{{l}_{2}}/hv}\]\[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-Cl+ClC{{H}_{2}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-Cl\] (iv) Chlorination of\[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{3}}\]\[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{3}}\xrightarrow[\Delta ]{C{{l}_{2}}/hv}C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-CH\] Thus, least monochlorination of \[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix} C{{H}_{3}} \\ | \end{smallmatrix}}{\mathop{C}}}\,-C{{H}_{3}}\]is possible
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