Cyclooctatetraene () contains exactly -electrons. Despite meeting the electron criteria for anti-aro — GOC and Organic Chemistry Basics Chemistry Question
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?
Answer: B
💡 Solution & Explanation
To avoid the immense thermodynamic instability associated with being anti-aromatic (having $4n\ \pi$ -electrons), cyclooctatetraene distorts from a planar octagon into a non-planar 'tub' shape. This breaks the continuous $\pi$ -overlap, rendering it non-aromatic.
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