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A cyclic ring molecule follows Hückel's rule when the number of its π(pi)-electrons equals 4n+2 where n is zero or any positive integer, although clearcut examples are really only established for values of n = 0 up to about n = 6

A furan structure is a planar 5 membered ring with one O atom in its ring on which one pi-pair is situated. This leaves another 2 pi-pair's for two double bonds, a total of 6 (3 pi-pairs) obeys Hückel's rule for the n=1 value.

Thus furan is aromatic as benzene (also n=1, 6 pi-electrons in 3 pi-pairs).

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In the furan structure, the oxygen atom has two lone pairs of electrons, not four. The presence of these lone pairs contributes to the overall aromaticity and stability of the furan ring. The two remaining valence electrons of oxygen are involved in forming a double bond with the adjacent carbon atom, allowing for the resonance stabilization characteristic of aromatic compounds. Thus, the structure is consistent with the bonding requirements of oxygen while maintaining the aromatic properties of furan.


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Furan does not typically undergo nucleophilic substitution reactions because of its aromatic nature, which offers stability due to delocalization of the pi electrons in the ring. This makes furan less reactive towards nucleophilic attack compared to non-aromatic compounds.


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