AFMC AFMC Solved Paper-2003

  • question_answer
    Which of the following product is obtained by treating 1-butyne with \[HgS{{O}_{4}}\]and\[{{H}_{2}}S{{O}_{4}}\]?

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

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

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

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

    Correct Answer: A

    Solution :

    Ethyne \[\xrightarrow[H{{g}^{2+}}]{HOH/{{H}_{2}}S{{O}_{4}}}\]aldehyde \[(C{{H}_{3}}CHO)\]all other alkyne \[\xrightarrow[H{{g}^{2+}}]{HOH/{{H}_{2}}S{{O}_{4}}}\]ketone \[HC\equiv CH+HOH\xrightarrow[{{H}_{2}}S{{O}_{4}}]{H{{g}^{2+}}}\] \[\underset{Vinyl\,\,alcohol}{\mathop{{{H}_{2}}C=CHOH}}\,\xrightarrow{\operatorname{Re}arrangement}\underset{Ethanal}{\mathop{C{{H}_{3}}CHO}}\,\] \[{{H}_{3}}C-C\equiv CH\xrightarrow[HOH/{{H}_{2}}S{{O}_{4}}]{H{{g}^{2+}}}\] \[{{H}_{3}}C-\underset{OH}{\mathop{\underset{|}{\mathop{C}}\,}}\,-C{{H}_{2}}\xrightarrow{\operatorname{Re}rrangement}{{H}_{3}}C-\underset{O}{\mathop{\underset{|\,|}{\mathop{C}}\,}}\,-C{{H}_{3}}\] \[\underset{1-butyne}{\mathop{{{H}_{3}}CC{{H}_{2}}C}}\,\equiv CH\xrightarrow[HOH/{{H}_{2}}S{{O}_{4}}]{H{{g}^{2+}}}\] \[{{H}_{3}}C-C{{H}_{2}}-\underset{OH}{\mathop{\underset{|}{\mathop{C}}\,}}\,=C{{H}_{2}}\] \[\xrightarrow{\operatorname{Re}arrangement}{{H}_{3}}C-C{{H}_{2}}-\underset{\begin{smallmatrix}  O \\  Bu\tan ne \end{smallmatrix}}{\mathop{\underset{|\,|}{\mathop{C}}\,}}\,-C{{H}_{3}}\]


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