WB JEE Medical WB JEE Medical Solved Paper-2012

  • question_answer
    Upon treatment with and aqueous NaOH, which of the following compounds will form iodoform?

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

    B)  \[C{{H}_{3}}C{{H}_{2}}COC{{H}_{2}}C{{H}_{3}}\]

    C)  \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}OH\]

    D)  \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}CH(OH)C{{H}_{3}}\]

    Correct Answer: D

    Solution :

     \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}CH(OH)C{{H}_{3}}\xrightarrow{[O]}\] \[\underset{\text{keto}\,\text{methyl}\,\text{group}}{\mathop{C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}COC{{H}_{3}}}}\,\] \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-C{{H}_{3}}+3{{I}_{2}}+4NaOH\to \] \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}\overset{O}{\mathop{\overset{||}{\mathop{C}}\,}}\,-ONa+\underset{\text{iodoform}}{\mathop{CH{{I}_{3}}}}\,\] \[+\,3{{H}_{2}}O+3NaI\]


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