CMC Medical CMC-Medical VELLORE Solved Paper-2010

  • question_answer
    Tertiary alcohols \[(3{}^\circ )\]having at least four carbon atoms upon drastic oxidation yield carboxylic acid with

    A)  one carbon atom less

    B)  two carbon atoms less

    C)  three carbon atoms less

    D)  All the above three options are correct

    E)  None of the above

    Correct Answer: B

    Solution :

                    A\[3{}^\circ \]alcohol is very difficult to oxidised because they dont have carbon bearing \[-H\] and \[-OH\]both the groups. However, when treated under drastic conditions, cleavage of \[C-C\] bond takes place. They form mixture of ketone and carboxylic acid contains two carbon atom lesser than the starting alcohol. \[\underset{t-butyl\,alcohol}{\mathop{C{{H}_{3}}-\underset{C{{H}_{3}}}{\overset{C{{H}_{3}}}{\mathop{\underset{\mathbf{|}}{\overset{\mathbf{|}}{\mathop{C}}}\,}}}\,-OH}}\,\xrightarrow[(Strong\,condition)]{4[O]}\underset{\begin{smallmatrix}  \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,acetone \\  (one\,\,carbon\,\,atom\,\,less) \end{smallmatrix}}{\mathop{C{{H}_{3}}-\overset{C{{H}_{3}}}{\mathop{\overset{\mathbf{|}}{\mathop{C}}\,}}\,=O}}\,\]\[\xrightarrow[(strong\,condition)]{4\,[O]}\underset{two\,\,carbon\,\,atoms\,less}{\mathop{C{{H}_{3}}COOH}}\,+C{{O}_{2}}+{{H}_{2}}O\]


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