Manipal Medical Manipal Medical Solved Paper-2015

  • question_answer
    An alkane (molecular weight = 86) on mono chlorination gives only two monochloro derivatives. One isomer (X) of this alkane is obtained on catalytic reduction of alkene (Y) which gives four monochloro derivatives. Isomer (X) is

    A) \[\begin{align}   & C{{H}_{3}}-C{{H}_{2}}-CH-C{{H}_{3}} \\  & | \\  & C{{H}_{2}}-C{{H}_{3}} \\ \end{align}\]

    B) \[\begin{align}   & C{{H}_{3}}-CH-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{3}} \\  & | \\  & C{{H}_{3}} \\ \end{align}\]

    C) \[\begin{align}   & C{{H}_{3}}-CH-CH-C{{H}_{3}} \\  & || \\  & C{{H}_{3}}C{{H}_{3}} \\ \end{align}\]

    D) \[\begin{align}   & C{{H}_{3}} \\  & | \\  & C{{H}_{3}}-C{{H}_{2}}-C-C{{H}_{3}} \\  & | \\  & C{{H}_{3}} \\ \end{align}\]

    Correct Answer: A

    Solution :

    \[Alkane\underrightarrow{Monochlorination}\underbrace{I+II}_{Isomers}\] Mol. Wt. \[=86\Rightarrow {{C}_{6}}{{H}_{14}}\] \[Y(alkene)\xrightarrow[reduction]{Catalytic}X(isomer\,\,of\,\,A)\] \[\xrightarrow{Monochlorination}4\,\,monochloro\,\,derivatives\] As X is isomer of A thus it should have molecular formula \[{{C}_{6}}{{H}_{14}}\] \[\begin{align}   & \overset{1}{\mathop{C{{H}_{3}}}}\,-\overset{{}}{\mathop{\overset{2}{\mathop{C{{H}_{2}}}}\,-\overset{3}{\mathop{CH}}\,-C{{H}_{2}}-C{{H}_{3}}}}\, \\  & | \\  & \underset{4}{\mathop{C{{H}_{3}}}}\, \\ \end{align}\] This isomer of hexane gives four monochloro  products on chlorination.


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