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Dolbier HW Solutions 296 - 290 REACTIONS OF ARENES...

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( h ) Pyridine reacts with electrophiles at C-3. It is less reactive than benzene, and the carbocation intermediate is less stable than the corresponding intermediate formed from benzene. 12.24 ( a ) Toluene is more reactive than chlorobenzene in electrophilic aromatic substitution reac- tions because a methyl substituent is activating but a halogen substituent is deactivating. Both are ortho, para-directing, however. Nitration of toluene is faster than nitration of chlorobenzene. Faster: Slower: ( b ) A fl uorine substituent is not nearly as strongly deactivating as a tri fl uoromethyl group. The reaction that takes place is Friedel Crafts alkylation of fl uorobenzene. Strongly deactivated aromatic compounds do not undergo Friedel
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