Chemistry Organic Chemistry Results Discussion

Overview

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Electrophilic bromination of an equimolar mixture of methylbenzene (toluene) and (trifluoromethyl)benzene with one equivalent of bromine (in the presence of FeBr₃) gives exclusively 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene.

1. Explain why none of the (trifluoromethyl)benzene reacts
2. Explain the regiochemical outcome of the reaction In other words, why are 1-bromo-2-methylbenzene and 1-bromo-4-methylbenzene formed from the toluene?
3. Electrophilic nitration of benzoic acid gives almost exclusively 3-nitrobenzoic acid. By drawing the appropriate resonance forms of the intermediate cations resulting from attack of [NO₂]⁺, explain this result.