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Dolbier HW Solutions 297 - 5 CH 3 than for R 5(CH 3 3 C G...

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An oxygen substituent directly attached to the ring strongly activates it toward electrophilic aromatic substitution. Phenyl acetate is much more reactive than benzene or methyl benzoate. Bromination of methyl benzoate requires more vigorous conditions; catalysis by iron(III) bro- mide is required for bromination of deactivated aromatic rings. ( d ) Acetanilide is strongly activated toward electrophilic aromatic substitution and reacts faster than nitrobenzene, which is strongly deactivated. ( e ) Both substrates are of the type and are activated toward Friedel Crafts acylation. Since electronic effects are comparable, we look to differences in steric factors and conclude that reaction will be faster for R
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Unformatted text preview: 5 CH 3 than for R 5 (CH 3 ) 3 C G . CH 3 CH 3 1 p-Xylene Acetyl chloride 2,5-Dimethylacetophenone CH 3 CCl O AlCl 3 CH 3 CH 3 C O CH 3 R R R 5 alkyl HNCCH 3 O Acetanilide o-Acetamidobenzene-sulfonic acid HNCCH 3 O SO 3 H 1 p-Acetamidobenzene-sulfonic acid HNCCH 3 O SO 3 H SO 3 H 2 SO 4 N O O 2 1 Nitrobenzene (Nitrogen is positively charged and is electron-withdrawing.) HNCCH 3 O Acetanilide (Lone pair on nitrogen can stabilize cyclohexadienyl cation intermediate.) Br 2 acetic acid OCCH 3 O OCCH 3 Br O OCCH 3 Br O 1 Phenyl acetate o-Bromophenyl acetate p-Bromophenyl acetate REACTIONS OF ARENES: ELECTROPHILIC AROMATIC SUBSTITUTION 291...
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