Dolbier HW Solutions 292

Dolbier HW Solutions 292 - FeCl 3 Cl 2 1 Br Bromobenzene Br...

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( c ) Toluene is more reactive than benzene in electrophilic aromatic substitution. A methyl sub- stituent is an ortho, para director. ( d )T r i f uoromethyl is deactivating and meta-directing. ( e ) Anisole is ortho, para-directing, strongly activated toward electrophilic aromatic substitution, and readily sulfonated in sulfuric acid. Sulfur trioxide could be added to the sulfuric acid to facilitate reaction. The para isomer is the predominant product. ( f ) Acetanilide is quite similar to anisole in its behavior toward electrophilic aromatic substitution. ( g )
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Unformatted text preview: FeCl 3 Cl 2 1 Br Bromobenzene Br Cl o-Bromochloro-benzene Br Cl p-Bromochloro-benzene H 2 SO 4 1 HNCCH 3 O Acetanilide HNCCH 3 O SO 3 H o-Acetamidobenzene-sulfonic acid HNCCH 3 O SO 3 H p-Acetamidobenzene-sulfonic acid H 2 SO 4 OCH 3 Anisole OCH 3 SO 3 H o-Methoxybenzene-sulfonic acid p-Methoxybenzene-sulfonic acid OCH 3 SO 3 H 1 Br 2 FeBr 3 CF 3 (Tri f uoromethyl)-benzene CF 3 Br m-Bromo(tri f uoromethyl)-benzene Br 2 FeBr 3 CH 3 Toluene CH 3 Br o-Bromotoluene p-Bromotoluene CH 3 Br 1 286 REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION...
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