BCECE Engineering BCECE Engineering Solved Paper-2010

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

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

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

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

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

    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,              \[\underset{\text{ethanal}}{\mathop{C{{H}_{3}}\overset{H}{\mathop{\overset{|}{\mathop{C}}\,}}\,=O}}\,+O=\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C}}\,}}\,-CH=O+\underset{\text{formaldehyde}}{\mathop{O=\overset{H}{\mathop{\overset{|}{\mathop{CH}}\,}}\,}}\,\] \[\xrightarrow{{}}C{{H}_{3}}CH=\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C}}\,}}\,-CH=C{{H}_{2}}\]


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