Which compound amongst the following is not an aromatic compound?
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Answer
(4) [figure]
Solution
As per NCERT (Hückel rule), a species is aromatic if it is cyclic and planar, has complete delocalisation of π electrons in the ring and contains (4n+2) π electrons.
(1) In the cyclopentadienyl anion every ring carbon is sp2 and there are 6 π electrons (n = 1), so it is aromatic.
(2) The cycloheptatrienyl (tropylium) cation is fully conjugated with 6 π electrons (n = 1), so it is aromatic.
(3) The cyclopropenyl cation is fully conjugated with 2 π electrons (n = 0), so it is aromatic.
(4) Cycloheptatriene has one sp3 CH2 carbon, so its π electrons are not delocalised over the whole ring, which makes it non-aromatic.
Answer: (4)