question_answer

An organic compound \[A({{C}_{4}}{{H}_{6}}Cl)\] on reaction with Na/diethyl ether gives a hydrocarbon, which on monochlorination gives only one chloro derivative. A is [Kerala PMT 2004]

A) t-butyl chloride

B) s-butyl chloride

C) Isobutyl chloride

D) n-butyl chloride

E) None of these

Correct Answer: A

Solution :

\[2C{{H}_{3}}-\underset{Cl\ \ \ \ \ \ \,}{\overset{C{{H}_{3}}\ \ \ \ }{\mathop{\underset{|}{\overset{|}{\mathop{C}}}\,-C{{H}_{3}}}}}\,\underset{2Na}{\mathop{\xrightarrow{\text{ether}}}}\,C{{H}_{3}}-\underset{C{{H}_{3}}}{\overset{C{{H}_{3}}}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}\,\,--}}}\,\underset{C{{H}_{3}}\ \ \ \ \ }{\overset{C{{H}_{3}}\ \ \ \ \,}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}\,-C{{H}_{3}}}}}\,+2NaCl\]