The benzene ring modify the reactivity of neighboring group in the benzylic position much like a double bond alters the reactivity of groups in the allylic position. benzylic cations, anions, as well as radicals are more stable than simple alkyl intermediates.
a) Utilize resonance structures to show the delocalization over four carbons of the positive charge, unpaired electrons and negative charge of benzeyl cations, radical, anion.
b) Tolunene reacts with bromine in the presence of light to give benzyl bromide. Intend mechanism for the reaction.