NEET AIPMT SOLVED PAPER SCREENING 2006

  • question_answer
                    In a set of reactions propionic acid yielded a compound D.                                                            \[C{{H}_{3}}C{{H}_{2}}COO\xrightarrow[{}]{SOC{{l}_{2}}}B\xrightarrow[{}]{N{{H}_{3}}}C\xrightarrow[B{{r}_{2}}]{KOH}D\]                 The structure of D would be:

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

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

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

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

    Correct Answer: D

    Solution :

                    For reaction,                 \[\underset{\begin{smallmatrix}   \\  'A' \end{smallmatrix}}{\mathop{C{{H}_{3}}C{{H}_{2}}COOH}}\,\underset{\begin{smallmatrix}  -S{{O}_{2}} \\  -HCl \end{smallmatrix}}{\mathop{\xrightarrow{SOC{{l}_{2}}}}}\,\underset{\begin{smallmatrix}   \\  'B' \end{smallmatrix}}{\mathop{C{{H}_{3}}C{{H}_{2}}COCl}}\,\]                 \[\underset{-NHCl}{\mathop{\xrightarrow{N{{H}_{3}}}}}\,\underset{'C'}{\mathop{C{{H}_{3}}C{{H}_{2}}CON{{H}_{2}}}}\,\underset{\begin{smallmatrix}  \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,+B{{r}_{2}} \\  (-2KBr-{{K}_{2}}C{{O}_{3}},  \\  +2{{H}_{2}}O) \end{smallmatrix}}{\mathop{\xrightarrow{4KOH}}}\,\underset{\begin{smallmatrix}  \,\,\,\,\,\,\,\,\,\,\,'D' \\  (Ethyl\,a\min e) \end{smallmatrix}}{\mathop{C{{H}_{3}}C{{H}_{2}}N{{H}_{2}}}}\,\]                 (Hofmann-Bromamide reaction)                 Hence, compound ?D? is \[C{{H}_{3}}-C{{H}_{2}}-N{{H}_{2}}.\]


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