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Multiple Choice
Which of the following compounds is aromatic?
A
Cyclohexane ()
B
Benzene ()
C
Cyclobutadiene ()
D
Cyclooctatetraene ()
Verified step by step guidance
1
Recall the criteria for aromaticity: a compound must be cyclic, planar, fully conjugated (p orbitals at every atom in the ring), and follow Hückel's rule, which states it must have (4n + 2) π electrons, where n is a non-negative integer (0, 1, 2, ...).
Analyze each compound to check if it meets these criteria. Start with cyclohexane (C\6H\12): it is cyclic but saturated (no double bonds), so it has no π electrons and is not aromatic.
Next, consider benzene (C\6H\6): it is cyclic, planar, has alternating double bonds providing 6 π electrons, and 6 fits Hückel's rule with n=1 (4(1)+2=6). Thus, benzene is aromatic.
Examine cyclobutadiene (C\4H\4): it is cyclic and conjugated with 4 π electrons, but 4 does not satisfy Hückel's rule (4n+2 ≠ 4 for any integer n). Also, it is antiaromatic or non-aromatic due to instability.
Finally, look at cyclooctatetraene (C\8H\8): although it has 8 π electrons, it is not planar in its usual conformation, so it does not have continuous overlap of p orbitals and is not aromatic.