Many conjugated ions can be reactive in more than one place. Resonance structures can help one predict where these sights of reactivity might be$.$

Draw all reasonable resonance structures for the ion below $($draw them vertical on the paper$).$ Then show the reaction product with the alkyl halide on the arrow and add mechanism arrows to show the movement of electrons. $[$Remember$,$ you can still think about these as Lewis acid $/$ base reactions $($from each resonance structure$)].$

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$H_{3}C-Br$

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$H_{3}C-Br$