________ defined a set of aromaticity criteria using molecular orbital simulations.
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August Kekulé
________ claimed that benzene is made up of six carbon atoms arranged in a ring, with one hydrogen atom connected to each.
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annulene
A(n) ________ is a cyclic hydrocarbon with constantly overlapping 2p orbitals.
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Benzene
________ is best represented as a resonance hybrid comprised of two resonance forms with the double bond positions inverted.
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hydroxyl group
A(n) ________ linked to a benzene ring is the distinguishing property of phenols.
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Polynuclear aromatic hydrocarbons
________ (PAHs) have several benzene rings.
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aromatic properties of benzene
The ________ are not shared by all cyclic hydrocarbons with alternating double bonds.
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single contributing
For ease of understanding, benzene is frequently shown as a(n) ________ structure or as a hexagon with a circle drawn on the interior.
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stable hypothetical contributing
The difference in energy between a resonance hybrid and the most ________ structure in which electron density is confined is referred to as resonance energy.
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phenoxide anion
Because the negative charge of the ________ is substantially delocalized within the aromatic ring as suggested by resonance contributing structures, phenols (pKa approximately 10) are more acidic than simple alcohols.
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Benzylic ethers
________ are useful because they can act as protective groups for the- OH groups of alcohols and phenols, as shown in the image attached.
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benzene ring
The ________ is identified as a substituent on a parent chain in compounds with various functional groups.
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molecular orbitals
Bonding ________ are located below the line, nonbonding ________ (if present) are located on the line, and antibonding ________ are located above the line.
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phenoxide anion
Ring substituents that lead to increased stability of the ________ enhance phenol acidity, whereas substituents that destabilize the ________ lower phenol acidity.
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carbon atoms
The ring's ________ are all sp2 hybridized.
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carbon atom
Each ________ also possesses a single unhybridized 2p orbital with a single electron.
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