State catalyzed reaction of the ethylbenzene with bromine

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1. Draw a detailed mechanism for the FeBr3-catalyzed reaction of the ethylbenzene with bromine, and show why the sigma complex (and the transition state leading to it) is lower in energy for substitution at the ortho and para position than it is for substitution at the meta position. 2. Styrene (vinylbenzene) undergoes electrophilic aromatic substitution much faster than benzene, and the products are found to be primarily ortho- and para-substituted styrenes. Use resonance forms of the intermediates to explain these results. 3. Propose a detailed mechanism for the bromination of ethoxybenzene to give o- and p-bromoethoxybenzene. 4. Draw all the resonance forms of the sigma complex for niraion of bromobenzene a he ortho, meta, and para positions. Point out why the inermediate for meta substitution is less stable than the other two.

Reference no: EM13164132

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