Question
Download Solution PDFWhich of the following compound is not aromatic?
Answer (Detailed Solution Below)
Detailed Solution
Download Solution PDFConcept:
Aromaticity of a compound can be decided by Huckel’s rule.
In cyclopentadienyl cation (A), resonance takes place.
Hence, is anti-aromatic.
Anti-aromaticity is a characteristic of a cyclic molecule with a π electron system that has higher energy due to the presence of 4n delocalised (π or lone pair) electrons in it.
Unlike aromatic compounds, which follow Hückel's rule ([4n + 2] π electrons) and are highly stable, anti-aromatic compounds are highly unstable and highly reactive.
Huckel’s rule as it has conjugated 4-electron system. Rest of the species are aromatic at each of them belongs to 6
-electron [(4n + 2)π, n = 1] system.
Huckel's rule estimates whether a planar ring molecule will have aromatic properties.
The Möbius-Huckel’s concept, a cyclic ring molecule follows Huckel’s rule when the number of its π-electron equals 4n + 2 where n is a non-negative integer.
Compounds (B), (C), (D) are containing 6πe- in complete conjugation and are aromatic
Compound (A) is anti-aromatic as it has 4πe in complete conjugation and doesn’t obey Huckel rule.
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