JEE Main & Advanced Chemistry Aldehydes, Ketones Question Bank Critical Thinking Aldehydes,

  • question_answer
    The conversion of acetophenone to acetanilide is best accomplished by using :                                  [UPSEAT 2004]

    A)                 Backmann rearrangement

    B)                 Curtius rearrangement

    C)                 Lossen rearrangement

    D)                 Hofmann rearrangement

    Correct Answer: A

    Solution :

               \[\overset{\overset{\,\,\,\,\,\,\,\,\,\,\,\,\,C{{H}_{3}}}{\mathop{\,\,\,\,\,\,\,\,\,\,\,|}}\,}{\mathop{{{C}_{6}}{{H}_{5}}-C=O}}\,+{{H}_{2}}NOH\xrightarrow[-{{H}_{2}}O]{}\underset{\underset{\text{methyl phenyl ketoxime}}{\mathop{\text{Acetophenone oxime or}}}\,}{\mathop{\overset{\overset{\,\,\,\,\,\,C{{H}_{3}}}{\mathop{\,|}}\,}{\mathop{{{C}_{6}}{{H}_{5}}-C=NOH}}\,}}\,\]\[\underset{\begin{smallmatrix}  \,\,\,\text{Backmann} \\  \text{rearrangement} \end{smallmatrix}}{\mathop{\xrightarrow{{{H}_{2}}S{{O}_{4}}}}}\,\underset{\text{Acetanilide}}{\mathop{{{C}_{6}}{{H}_{5}}NHCOC{{H}_{3}}}}\,\]


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