Question

Which one of the following is likely to give a precipitate with $AgN{O}_3$ solution?

• A. $C{H}_2=CHCl$
• B. $CC{l}_4$
• C. $CHC{l}_3$
• D. $(C{H}_3{)}_{3}CCl$

Answer 1

The correct option is D $(C{H}_3{)}_{3}CCl$

$(C{H}_3{)}_{3}CCl$ gives a precipitate with $AgN{O}_3$ solution because it forms stable carbocation. (i.e. tertiary) that readily combines with $AgN{O}_3$ to give precipitates of $AgCl$.
$\left(C{H}_3{)}_{3}CCl\right)+AgN{O}_3\to (C{H}_3{)}_3{C}^{+}+AgCl$
$C{H}_2=CHCl$ forms unstable carbocation. Hence, it does not readily react with $AgN{O}_3$.