Dolbier HW Solutions 594

Dolbier HW Solutions 594 - 688 PHENOLS (e) The hydroxyl...

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( e ) The hydroxyl group, as the most activating substituent, controls the orientation of elec- trophilic aromatic substitution. Bromination takes place ortho to the hydroxyl group. ( f ) Oxidation of hydroquinone derivatives ( p -dihydroxybenzenes) with Cr(VI) reagents is a method for preparing quinones. ( g ) Aryl esters undergo a reaction known as the Fries rearrangement on being treated with aluminum chloride, which converts them to acyl phenols. Acylation takes place para to the hydroxyl in this case. ( h ) Nucleophilic aromatic substitution takes place to yield a diaryl ether. The nucleophile is the
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