Question
Bottles containing $${C_6}{H_5}I$$ and $${C_6}{H_5}C{H_2}I$$ lost their original labels. They were labelled $$A$$ and $$B$$ for testing. $$A$$ and $$B$$ were separately taken in test tubes and boiled with $$NaOH$$ solution. The end solution in each tube was made acidic with dilute $$HN{O_3}$$ and then some $$AgN{O_3}$$ solution was added. Substance B gave a yellow precipitate. Which one of the following statements is true for this experiment ?
A.
$$A$$ and $${C_6}{H_5}C{H_2}I$$
B.
$$B$$ and $${C_6}{H_5}I$$
C.
Addition of $$HN{O_3}$$ was unnecessary
D.
$$A$$ was $${C_6}{H_5}I$$
Answer :
$$A$$ was $${C_6}{H_5}I$$
Solution :
\[\begin{align}
& {{C}_{6}}{{H}_{5}}I\xrightarrow{NaOH}{{C}_{6}}{{H}_{5}}ONa\xrightarrow{HN{{O}_{3}}/{{H}^{+}}} \\
& {{C}_{6}}{{H}_{5}}OH\xrightarrow{AgN{{O}_{3}}}\text{No}\,\,\text{yellow}\,\,ppt. \\
& {{C}_{6}}{{H}_{5}}C{{H}_{2}}I\xrightarrow{NaOH}{{C}_{6}}{{H}_{5}}C{{H}_{2}}ONa\xrightarrow{HN{{O}_{3}}/{{H}^{+}}} \\
& {{C}_{6}}{{H}_{5}}C{{H}_{2}}OH\xrightarrow{AgN{{O}_{3}}}.\,\text{yellow}\,\,ppt. \\
\end{align}\]
Since benzyl iodide gives yellow ppt. hence this is
compound $$B$$ and $$A$$ was phenyl iodide \[\left( {{C}_{6}}{{H}_{5}}I \right).\]