Cyclooctatetraene () contains exactly -electrons. Despite meeting the electron criteria for anti-aromaticity, it exhibits the chemical behavior of a typical non-aromatic polyene. What is the primary p

Question

Cyclooctatetraene ($C_8H_8$) contains exactly $8\ \pi$ -electrons. Despite meeting the $4n$ electron criteria for anti-aromaticity, it exhibits the chemical behavior of a typical non-aromatic polyene. What is the primary physical reason for this?

Prashant Kotian · Accepted Answer

Correct answer: B. To avoid the immense thermodynamic instability associated with being anti-aromatic (having -electrons), cyclooctatetraene distorts from a planar octagon into a non-planar 'tub' shape. This breaks the continuous -overlap, rendering it non-aromatic.

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