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Dolbier HW Solutions 535 - 3 O(CH 3 3 CCl AlCl 3...

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( b ) Acetanilide is a reactive substrate toward electrophilic aromatic substitution. An acetamido group is ortho, para-directing. ( c ) Sulfonation of the ring occurs. ( d ) Bromination of the ring takes place. ( e ) Acetanilide undergoes Friedel Crafts alkylation readily. ( f ) Friedel Crafts acylation also is easily carried out. Acetanilide Acetyl chloride ortho isomer C 6 H 5 NHCCH 3 O CH 3 CCl O AlCl 3 p -Acetamidoacetophenone O NHCCH 3 CCH 3 O Acetanilide tert -Butyl chloride ortho isomer C 6 H
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Unformatted text preview: 3 O (CH 3 ) 3 CCl AlCl 3 p-tert-Butyl-acetanilide O NHCCH 3 C(CH 3 ) 3 Acetanilide p-Bromoacetanilide 1 C 6 H 5 NHCCH 3 ortho isomer O Br 2 acetic acid O NHCCH 3 Br Acetanilide p-Acetamidobenzenesulfonic acid 1 C 6 H 5 NHCCH 3 O SO 3 H 2 SO 4 O NHCCH 3 SO 3 H ortho isomer Acetanilide o-Nitroacetanilide p-Nitroacetanilide 1 C 6 H 5 NHCCH 3 O HNO 3 H 2 SO 4 O NHCCH 3 NO 2 O NHCCH 3 NO 2 AMINES 629...
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