Why is benzyl chloride reactive in both tests, whereas bromobenzene is unreactive?

3 answers

Benzyl chloride is an alkyl (not aromatic) halide. The electron density around the halogen is not delocalized effectively. That makes it easier for the halogen to leave as an anion and form silver or some other halide.
Bromobenzene has lower electron density because of delocalization of its charge by the π-electron system in the adjacent benzene ring. That makes it more difficult for Br to leave as an anion.
wrong buddy.....
because of resonance and adjacent π-system stabilizing with the atom....it allows the anion to leave easier :)
no your rong pal
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