JEE Main & Advanced Chemistry Hydrocarbons / हाइड्रोकार्बन Question Bank Alkane

  • question_answer
    Sample of 2, 3-dibromo-3-methylpentane is heated with zinc dust. The resulting product is isolated and heated with HI in the presence of phosphorus. Indicate which is the structure that represent the final organic product formed in the reaction [CBSE PMT 1991]

    A) \[\underset{C{{H}_{3}}}{\mathop{\underset{|\,\,\,\,\,\,\,}{\mathop{C{{H}_{3}}-C{{H}_{2}}-CH-C{{H}_{2}}-C{{H}_{3}}}}\,}}\,\]

    B) \[\overset{\,\,C{{H}_{3}}}{\mathop{\overset{|\,\,\,\,\,\,\,}{\mathop{C{{H}_{2}}=CH-CH-C{{H}_{2}}-C{{H}_{3}}}}\,}}\,\]

    C) \[\underset{C{{H}_{3}}}{\mathop{\underset{|\,\,\,\,\,\,\,}{\mathop{C{{H}_{3}}-CHI-CH-C{{H}_{2}}-C{{H}_{3}}}}\,}}\,\]

    D) \[\underset{C{{H}_{3}}}{\mathop{\underset{|\,\,\,\,\,\,\,}{\mathop{C{{H}_{2}}=CH-C(I)-C{{H}_{2}}-C{{H}_{3}}}}\,}}\,\]

    Correct Answer: A

    Solution :

               \[\underset{\text{2,3}-\text{dibromo}-\text{3}-\text{methyl}\,\text{pentane}\,\,\,\,\,\,\,\,\,\,}{\mathop{C{{H}_{3}}-\underset{\underset{Br\,\,}{\mathop{\,|\,\,\,\,\,}}\,}{\mathop{CH}}\,-\underset{\underset{Br}{\mathop{|\,\,}}\,\,\,\,\,}{\overset{\overset{C{{H}_{3}}}{\mathop{|\,\,\,\,\,\,\,}}\,}{\mathop{C-}}}\,C{{H}_{2}}-C{{H}_{3}}+Zn\to }}\,\]                    \[\underset{\text{HI}\,+\,{{\,}_{\downarrow }}\,\,\,\text{Red}\,\text{P}\,\left( \text{Reduction} \right)}{\mathop{C{{H}_{3}}-CH=\overset{\overset{C{{H}_{3}}}{\mathop{|\,\,\,\,\,\,\,\,}}\,}{\mathop{C\,-\,\,}}\,C{{H}_{2}}-C{{H}_{3}}+ZnB{{r}_{2}}}}\,\]          \[\underset{\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\text{3}-\text{Methyl}\,\text{pentane}}{\mathop{C{{H}_{3}}-C{{H}_{2}}-\underset{\underset{C{{H}_{3}}}{\mathop{|\,\,\,\,\,\,\,\,}}\,}{\mathop{CH\,\,}}\,-C{{H}_{2}}-C{{H}_{3}}}}\,\]


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