Question

With alcoholic silver nitrate benzyl chloride forms precipitate of silver chloride but chlorobenzene does not do so explain

Answer 1

When AgNO3 reacts with the halides they form insoluble silver halides such as silver chloride , silver bromide and silver iodide. but silver fluoride is soluble, hence no ppt formed.

Answer 2

Answer:

Benzyl chloride would give precipitate with AgNO3 solution. You see, only those halides which can give a stable carbocation at the carbon to which the halogen atom is attached, can give precipitate of Silver halide with Silver nitrate solution.

Now which of them can give a stable carbocation?

Phenyl carbocation is a highly unstable and high energy specie, so Chlorobenzene can't give precipitate of AgCl.

But, carbocation furnished by benzyl chloride is highly stable due to resonance and so, it can give a precipitate of AgCl.