One of the following compounds is much more stable than the other two. Classify each as aromatic, antiaromatic, or nonaromatic.

Verified step by step guidance

1. Step 1: Recall the criteria for aromaticity. A compound is aromatic if it satisfies the following conditions: (1) It is cyclic, (2) It is planar, (3) It has a conjugated π-electron system, and (4) It follows Hückel's rule, which states that the molecule must have (4n + 2) π-electrons, where n is a non-negative integer.
2. Step 2: Analyze heptalene. Heptalene is cyclic and conjugated, but it does not satisfy Hückel's rule because it has 8 π-electrons, which is not of the form (4n + 2). Instead, it falls under the category of antiaromatic compounds because it has (4n) π-electrons and is planar.
3. Step 3: Analyze azulene. Azulene is cyclic, planar, and conjugated. It has 10 π-electrons, which satisfies Hückel's rule (4n + 2, where n = 2). Therefore, azulene is aromatic and much more stable due to aromatic stabilization.
4. Step 4: Analyze pentalene. Pentalene is cyclic and conjugated, but it has 8 π-electrons, which does not satisfy Hückel's rule. Additionally, it is antiaromatic because it has (4n) π-electrons and is planar, leading to instability.
5. Step 5: Conclude the classification. Heptalene and pentalene are antiaromatic and unstable, while azulene is aromatic and much more stable due to aromatic stabilization.

Key Concepts

Aromaticity

Aromatic compounds are cyclic, planar molecules with a ring of resonance that follow Hückel's rule, which states they must have 4n + 2 π electrons (where n is a non-negative integer). This unique electron configuration leads to increased stability due to delocalization of electrons across the ring, making aromatic compounds particularly stable compared to nonaromatic and antiaromatic compounds.

Antiaromaticity

Antiaromatic compounds are also cyclic and planar but contain 4n π electrons, which leads to instability due to the unfavorable electron delocalization. This instability arises because the electron configuration does not satisfy Hückel's rule, resulting in increased energy and reactivity compared to both aromatic and nonaromatic compounds.

Nonaromaticity

Nonaromatic compounds do not meet the criteria for aromaticity or antiaromaticity. They may be acyclic, lack planarity, or have an insufficient number of π electrons. As a result, nonaromatic compounds typically exhibit stability levels that fall between aromatic and antiaromatic compounds, depending on their specific structural features.