BCECE Medical BCECE Medical Solved Papers-2010

  • question_answer
    Which set of products is expected on reductive ozonolysis of the following diolefin? \[C{{H}_{3}}CH=\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,-CH=C{{H}_{2}}\]

    A)  \[C{{H}_{3}}CHO;C{{H}_{3}}COCH=C{{H}_{2}}\]

    B)  \[C{{H}_{3}}CH=\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\mathop{C}}\,-CHO;C{{H}_{2}}O\]

    C)  \[C{{H}_{3}}CHO;C{{H}_{3}}COCHO;C{{H}_{2}}O\]

    D)  \[C{{H}_{3}}CHO;C{{H}_{3}}COC{{H}_{2}};C{{H}_{2}}O\]

    Correct Answer: C

    Solution :

    When an alkene is subjected to reductive ozonolysis, the double bond breaks and two O atoms are attached to the double bonded carbon atoms in the final product. Thus, \[\underset{ethanal}{\mathop{C{{H}_{3}}\overset{\begin{smallmatrix}  H \\  | \end{smallmatrix}}{\mathop{C}}\,=O}}\,+O=\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,-CH=O+\,\,\underset{formaldehyde}{\mathop{O=\overset{\begin{smallmatrix}  H \\  | \end{smallmatrix}}{\mathop{C}}\,H}}\,\]              \[\xrightarrow{{}}\,\,\,C{{H}_{3}}CH=\overset{\begin{smallmatrix}  C{{H}_{3}} \\  | \end{smallmatrix}}{\mathop{C}}\,-CH=C{{H}_{2}}\]


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