JEE Main & Advanced Chemistry Haloalkanes and Haloarenes Question Bank Critical Thinking Haloalkanes

  • 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 :

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

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