Bottles containing $\mathrm{C}_6 \mathrm{H}_5$ l and $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{I}$…

Bottles containing $\mathrm{C}_6 \mathrm{H}_5$ l and $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{I}$ lost their original labels. They were labelled $\mathrm{A}$ and $\mathrm{B}$ for testing $\mathrm{A}$ and $\mathrm{B}$ were separately taken in test tubes and boiled with $\mathrm{NaOH}$ solution. The end solution in each tube was made acidic with dilute $\mathrm{HNO}_3$ and then some $\mathrm{AgNO}_3$ solution was added. Substance B gave a yellow precipitate. Which one of the following statements is true for this experiment?
  1. A and $\mathrm{C}_6 \mathrm{H}_5 \mathrm{CH}_2 \mathrm{I}$
  2. $B$ and $\mathrm{C}_6 \mathrm{H}_5 \mathrm{I}$
  3. Addition of $\mathrm{HNO}_3$ was unnecessary
  4. A was $\mathrm{C}_6 \mathrm{H}_5 \mathrm{I}$

Solution

$\mathrm{C}_6 \mathrm{H}_5 \mathrm{I}$ will not respond to silver nitrate test because $\mathrm{C}$-I bond has a partial double bond character.

Asked in: JEE Main 2003

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