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Electrophillic Aromatic Substitution

bauerle2
in Organic Chemistry

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I recently completed a lab dealing with electrophilic bromination and nitration of phenacetin. The bromination product revealed a bromine group ortho to the ethoxy substituent, while the nitration product revealed a nitro group ortho to the acetamide group. I know both the alkoxy and acetamide group are ortho-para directors, so why do the nitro and bromo groups substitute at different positions on the aromatic ring? Is this a result of steric effects or something different?

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