Benzene has delocalised pi- electrons spread over all 6 Carbon atoms in the ring structure. Therefore, there is insufficient electron density above and below any two carbon atoms in the structure so benzene cannot induce a dipole within a bromine molecule.
However, within Cyclohexene the delocalised pi- electrons are localised above and below the two specific Carbon atoms in the double bond, which means there is a region of high electron density within Cyclohexene. Cyclohexene is able to induce a dipole within a bromine molecule, allowing it to react.