JIPMER Jipmer Medical Solved Paper-1995

  • question_answer
    An organic halide, shaken with aqueous \[NaOH\] followed by the addition of dil. \[HN{{O}_{3}}\] and silver nitrate solution, gave white precipitate. The substance may be:

    A)  \[{{C}_{6}}{{H}_{4}}(C{{H}_{3}})Br\]

    B)                         \[{{C}_{6}}{{H}_{5}}C{{H}_{2}}Cl\]           

    C)         \[{{C}_{6}}{{H}_{5}}Cl\]

    D)                                         none of these

    Correct Answer: B

    Solution :

    Benzyl chloride is quite reactive hallide. It gives \[NaCl\] when reacts with (aq.) \[NaOH,\]which gives white precipitate with \[AgN{{O}_{3}}\]solution. Benzyl chloride also give white precipitate with \[AgN{{O}_{3}}\]solution directly. \[{{C}_{6}}{{H}_{5}}C{{H}_{2}}Cl+NaOH\xrightarrow{{}}{{C}_{6}}{{H}_{5}}C{{H}_{2}}OH+NaCl\] \[NaCl+AgN{{O}_{3}}\xrightarrow{{}}NaN{{O}_{3}}+\underset{\text{White}\,\text{ppt}\text{.}}{\mathop{AgCl\downarrow }}\,\]


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