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Which of the following compounds does NOT satisfy the criteria for aromaticity?

1. Thiophene
2. Cyclohexadiene
3. Tropylium cation
4. Furan

Correct answer: Cyclohexadiene

Solution

Cyclohexadiene has only two double bonds (4 pi electrons) and contains sp3-hybridised CH2 groups that break the conjugation, so it is neither fully conjugated nor does it satisfy Huckel's rule, making it non-aromatic.

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