BVP Medical BVP Medical Solved Paper-2008

  • question_answer
    tert-butyl methyl ether on heating with anhydrous HI in ether gives

    A)  \[C{{H}_{3}}OH+{{(C{{H}_{3}})}_{3}}Cl\]

    B)  \[C{{H}_{3}}I+{{(C{{H}_{3}})}_{3}}COH\]

    C)  \[C{{H}_{3}}I+{{(C{{H}_{3}})}_{3}}Cl\]

    D)  None of the above

    Correct Answer: B

    Solution :

                    Here, ether is the solvent. Being less polar, it favours \[{{S}_{N}}2\] reaction and the nucleophile \[{{I}^{-}}\] attacks the \[{{1}^{o}}\] carbon of \[C{{H}_{3}}\].\[{{I}^{-}}+C{{H}_{3}}\overset{\oplus }{\mathop{\underset{H}{\mathop{\underset{|}{\mathop{O}}\,}}\,}}\,-\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{\underset{C{{H}_{3}}}{\mathop{\underset{|}{\mathop{C}}\,}}\,}}\,}}\,-C{{H}_{3}}\]\[\xrightarrow{{{S}_{N}}2}C{{H}_{3}}I+\underset{C{{H}_{3}}}{\mathop{\underset{|}{\mathop{\overset{C{{H}_{3}}}{\mathop{\overset{|}{\mathop{C{{H}_{3}}-C-OH}}\,}}\,}}\,}}\,\]


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