교과서 질문
(i) Classify the following molecules as aromatic, nonaromatic, or antiaromatic.
(ii) For aromatic molecules, solve for n in Hückel’s rule. For all other molecules, explain which rule of aromaticity is being broken.
(e)
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18. Aromaticity
Aromatic Hydrocarbons
Multiple Choice
Which of the following compounds is aromatic?
A
(cyclohexane)
B
(benzene)
C
(heptane)
D
(cyclopentene)
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검증된 단계별 안내1
Recall the definition of aromaticity: a compound is aromatic if it is cyclic, planar, fully conjugated (p orbitals at every atom in the ring), and follows Hückel's rule, which states it must have \(4n + 2\) π electrons, where \(n\) is a non-negative integer.
Examine each compound to check if it meets these criteria. Start with cyclohexane (\(C_6H_{12}\)): it is cyclic but saturated (only single 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 a conjugated π system, and contains 6 π electrons. Check if 6 fits Hückel's rule by solving \(4n + 2 = 6\).
Look at heptane (\(C_7H_{16}\)): it is an acyclic alkane (no ring), so it cannot be aromatic.
Finally, analyze cyclopentene (\(C_5H_{10}\)): it is cyclic and has one double bond, but it is not fully conjugated around the ring and does not have the required number of π electrons to satisfy Hückel's rule, so it is not aromatic.
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