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![[Post New]](/templates/default/images/icon_minipost_new.gif) 23 Nov 2007 17:36:43 IST
Accepted Answer [?]
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The diazonium coupling reaction can take place between:
i) a strong electrophile and a strong nucleophile,
ii) a strong electrophile and a weak nucleophile,
iii) a weak electrophile and a strong nucleophile.
This reaction cannot take place between a weak electrohphile and a weak nucleophile. Benzenediazonium ion is a very weak electrophile; it is much weaker than NO2 +, Br+,etc. Being a very weak electrophile, benzenediazonium ion cannot couple with anisole, a weak nucleophile. The presence of an electron withdrawing group at the o- or p- position with respect to the diazonium group increases the electrophilicity of the b -N atom of the diazonium group. As the electrophilicity increases, the rate of coupling reaction increases. Thus 2,4-dinitrobenzenediazonium ion couples with anisole and 2,4,6-trinitrobenzene-diazonium ion even couples with mesitylene, a very weak nucleophile.
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