1.

(a)Azulene has an appreciabel dipole moment.Write the reasonance structure that explains the dipole moment and its aromaticity. (b)In the cse of halogen-substituted azulenes,a halogen atom onC-6can be displace bynucleophile while one onC-1is unreactive towards nucleophile .Rationalise this differemce in behaviou.

Answer»

Solution :
The major CONTRIBUTION to the HYBRID must be one that involves charge separation ,having aromatic five-and seven-membered rings.
(b)
`ArSN` intermediate reaction is favoured by five-membered ring WOTH cyclopentadienyl anion character(aromatic).
In the second case`BAR(e)`discoalisation into the other (seven-membered)ring result in eight`bar(e)`-in that ring ,which DOESNOT stablise it.


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