Dolbier HW Solutions 567

Dolbier HW Solutions 567 - 661 ARYL HALIDES(i The aromatic...

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( i ) The aromatic ring of N , N -dimethylaniline is very reactive and is attacked by p -chlorobenzene- diazonium ion. ( j ) Hexa f uorobenzene undergoes substitution of one of its f uorines on reaction with nucleo- philes such as sodium hydrogen sul F de. 23.12 ( a ) Since the tert -butoxy group replaces f uoride at the position occupied by the leaving group, substitution likely occurs by the addition elimination mechanism. ( b ) In nucleophilic aromatic substitution reactions that proceed by the addition elimination mechanism, aryl f uorides react faster than aryl bromides. Because the aryl bromide is more reactive in this case, it must be reacting by a different mechanism, which is most likely elimination addition. 23.13 ( a ) Two benzyne intermediates are equally likely to be formed. Reaction with amide ion can
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