Benzene is a planar, aromatic hydrocarbon compound with the chemical formula C6H6. It is a key building block in organic chemistry and has a unique resonance structure that contributes to its stability and reactivity.
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Benzene has a unique hexagonal structure with alternating single and double carbon-carbon bonds, which is stabilized by the delocalization of its pi electrons.
The Hückel 4n + 2 rule states that planar, cyclic, conjugated systems with (4n + 2) pi electrons are aromatic, which applies to benzene with its 6 pi electrons.
Benzene exhibits high stability and low reactivity compared to other alkenes due to its aromatic nature, which is a result of its resonance stabilization.
The degree of unsaturation for benzene is 4, calculated using the formula: Degree of Unsaturation = (2C + 2 - H + N) / 2, where C is the number of carbon atoms, H is the number of hydrogen atoms, and N is the number of nitrogen atoms.
Benzene and its derivatives show characteristic signals in 13C NMR spectroscopy, with the carbon atoms appearing around 128 ppm, reflecting the aromatic nature of the compound.
Review Questions
Explain how the resonance structure of benzene contributes to its stability and reactivity.
The resonance structure of benzene, with its alternating single and double carbon-carbon bonds, allows for the delocalization of the pi electrons throughout the entire ring. This delocalization results in the stabilization of the molecule, making benzene more stable and less reactive compared to other alkenes. The resonance also affects the reactivity of benzene, as the delocalized pi system influences the way it undergoes electrophilic aromatic substitution reactions.
Describe the Hückel 4n + 2 rule and its application to the aromaticity of benzene.
The Hückel 4n + 2 rule states that planar, cyclic, conjugated systems with (4n + 2) pi electrons are considered aromatic. In the case of benzene, it has 6 pi electrons, which satisfies the 4n + 2 condition (where n = 1). This means that benzene is an aromatic compound, and its planar, cyclic, and conjugated structure contributes to its enhanced stability and characteristic reactivity compared to non-aromatic compounds.
Analyze how the degree of unsaturation and the 13C NMR spectrum of benzene are related to its aromatic nature.
The degree of unsaturation for benzene is calculated to be 4, indicating the presence of four rings and/or multiple bonds in the molecule. This high degree of unsaturation is a result of benzene's aromatic structure, with its alternating single and double bonds. Additionally, the 13C NMR spectrum of benzene shows characteristic signals around 128 ppm, reflecting the deshielding of the carbon atoms due to the delocalized pi system. This 13C NMR signature is a clear indication of the aromatic nature of benzene and its unique electronic structure.
The property of certain cyclic conjugated compounds, such as benzene, that exhibit enhanced stability and resistance to disruption of the pi electron system.
Multiple Lewis structures that can be drawn for a molecule, representing the delocalization of electrons and contributing to the overall stability of the compound.