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Choose the Best Answer · Q22

Q.Which one of the following is non aromatic?

(a) benzene
(b) naphthalene
(c) thiophene (the five-membered S-heterocycle)
(d) cyclopentadiene (the five-membered ring with one sp3 CH2 and two C=C double bonds)
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Step 1. Benzene: planar, 6 fully delocalised pi electrons, satisfies 4n+2 with n=1 -- aromatic.

Step 2. Naphthalene: planar, 10 fully delocalised pi electrons, satisfies 4n+2 with n=2 -- aromatic.

Step 3. Thiophene: a planar five-membered ring with two C=C double bonds (4 pi electrons) PLUS one lone pair on the ring sulfur donated into the pi system, giving 6 fully delocalised pi electrons in total, satisfying 4n+2 with n=1 -- aromatic (a classic aromatic heterocycle, directly analogous to how benzene's own electron count arises). …

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