See image — GOC and Organic Chemistry Basics Chemistry Question

💡 Solution & Explanation

# Anti-aromatic Compound Identification **Anti-aromatic criterion:** A cyclic, planar compound with $(4n+2)$ π electrons is aromatic; $(4n)$ π electrons makes it anti-aromatic. **Analysis of each option:** **(A) Benzocycloheptatrienyl anion** ($C_{13}H_{11}^-$) - 10π electrons (benzene ring contributes 6π, three C=C bonds contribute 4π) - $(4n+2)$ form with $n=2$ → **Aromatic** ✓ **(B) Dibenzocyclooctatetraene** ($C_{16}H_{12}$) - 14π electrons (two benzene rings contribute 12π, two C=C bonds contribute 2π) - $(4n+2)$ form with $n=3$ → **Aromatic** ✓ **(C) Naphthalene** ($C_{10}H_8$) - 10π electrons total - $(4n+2)$ form with $n=2$ → **Aromatic** ✓ **(D) Pyrrole** ($C_4H_5N$) - 6π electrons (nitrogen contributes 2 lone pair electrons + 2 from C=C bonds + 2 from C=C bonds) - $(4n+2)$ form with $n=1$ → **Aromatic** ✓ **Answer: Option (C)** is not anti-aromatic because naphthalene is **aromatic**, not anti-aromatic. All options are either aromatic or anti-aromatic; however, the question likely seeks which one is *not anti-aromatic*—meaning aromatic—making naphthalene the correct answer as it is purely aromatic with no anti-aromatic character.