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  4. An organic halide, shaken with aqueous NaOH followed by the addition of dil. HNO3 and silver nitrate solution, gave white precipitate. The substance may be:

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Q. 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:

JIPMERJIPMER 1995

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 }}\, $