JCECE Engineering JCECE Engineering Solved Paper-2005

  • question_answer
    Which of the following compounds forms an addition compound with \[C{{H}_{3}}MgBr\], which on hydrolysis produce a secondary alcohol?

    A) \[HCHO\]                            

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

    C) \[C{{H}_{3}}OC{{H}_{3}}\]                           

    D) \[C{{H}_{3}}COC{{H}_{3}}\]

    Correct Answer: B

    Solution :

    Key Idea: \[HCHO+Grignard\,\,reagent\xrightarrow{hydrolysis}\] \[{{1}^{o}}alcohol\] \[Any\,\,other\,\,aldehdye+Grignard\text{ }reagent\] \[\xrightarrow{Hydrolysis}{{2}^{o}}alcohol\] \[Ketone+Grignard\,\,reagent\]\[\xrightarrow{Hydrolysis}\] \[{{3}^{o}}alcohol\] \[\underset{(a)}{\mathop{HCHO}}\,\underset{\begin{smallmatrix}  \,\,\,\,\,\,\,(b) \\  aldehyde \end{smallmatrix}}{\mathop{C{{H}_{3}}CHO}}\,\underset{\begin{smallmatrix}  \,\,\,(c) \\  ether \end{smallmatrix}}{\mathop{C{{H}_{3}}OC{{H}_{3}}}}\,\underset{\begin{smallmatrix}  \,\,\,(d) \\  ketone \end{smallmatrix}}{\mathop{C{{H}_{3}}COC{{H}_{3}}}}\,\] \[\therefore \,\,C{{H}_{3}}CHO\]is correct choice. \[C{{H}_{3}}CHO+C{{H}_{3}}MgBr\xrightarrow{{}}C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  OMgBr \\  | \end{smallmatrix}}{\mathop{C}}}\,-H\] \[\underset{{{2}^{o}}alcohol}{\mathop{C{{H}_{3}}-\underset{\begin{smallmatrix}  | \\  C{{H}_{3}} \end{smallmatrix}}{\overset{\begin{smallmatrix}  \downarrow {{H}_{2}}O \\  OH  \\  | \end{smallmatrix}}{\mathop{C}}}\,-H}}\,\]


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