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| bond order between adjacent C atoms in a benzene ring |
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Definition
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| how the bond lengths between adjacent C's in benzene compare to typical single and double bonds |
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| shorter than single bonds, but longer than double bonds |
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| benzoid aromatic compounds |
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| why benzene and other aromatic compounds have unusal reaction properties |
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Definition
| because aromatic compounds are more stable than they would be if stabilized by resonance |
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| illustration of the stability of benzene compared to alkene |
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| bond angles in benzene rings |
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| how the pi electrons are distributed in a benzene |
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Definition
all the unhybridized p orbitals align and overlap
[image] |
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| the type of rxn that normally takes place on a benzene ring |
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the product that does not result from this reaction
[image] |
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| the molar heat of hydrogenation of benzene compared to that of some other 6-membered rings |
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Definition
cyclic hydrocarbons with alternating single and double bonds
[image] |
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| the π molecular orbitals of benzene, viewed from above |
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| the π1 energy level of benzene |
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| the π2 energy level of benzene |
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| the π3 energy level of benzene |
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| the π*4 energy level of benzene |
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| the π*5 energy level of benzene |
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| the π*6 energy level of benzene |
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| energy diagram of benzene |
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| molecular orbitals or cyclobutadiene |
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| energy diagram of cyclobutadiene |
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Definition
the molecular orbital energy diagram of a completely conjugated cyclic system has the same regular polygonal shape as the compound, with 1 vertex (the all-bonding MO) at the bottom
[image] |
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| criteria for a ring to be aromatic |
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Definition
1: cyclic
2: planar
3: unhybridized p orbital at each ring atom
4: has 4n + 2 π electrons (n = integer (0, 1, 2, 3,...)) |
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Definition
| cyclic, planar, and has unhybridized P orbitals at each ring atom, but wrong number of π electrons |
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| what antiaromaticity does to a ring |
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Definition
| makes it less stable and increases the electron energy |
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| nonaromatic aka aliphatic |
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Definition
| does not have a continuous, overlapping ring of p orbitals |
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| molecular orbitals of aromatic rings compared to those of antiaromatic rings |
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| molecular orbitals for 5-membered carbocations and carbanions |
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| compound that contains a ring of sp2-hybridized atoms other than C, such as O, N, and S |
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| the way electrons are distributed in pyridine |
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| pyridine acting as a base |
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| how electrons are distributed in pyrrole |
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| why pyrrole is a weak base but protonated pyrrole is a strong acid |
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Definition
| because the N becomes sp3-hybridized, thus non-planar, when it abstracts a proton
[image] |
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| basic and non-basic N atoms in an aromatic ring |
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| imidazole protonating and deprotonating |
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| how electrons are distributed in some 5-membered heterocycles |
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| polynuclear aromatic hydrocarbons |
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Definition
| aromatic compounds composed of 2 or more benzene rings |
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| what happens when the number of fused benzene rings increases? |
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Definition
-resonance energy per ring decreases
-compounds become more reactive |
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| how benzo[a]pyrene, a polynuclear aromatic hydrocarbon, damages DNA |
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Definition
the benzene ring as a substituent
[image] |
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the 7-C unit containing the benzene ring and the adjacent methylene
[image] |
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| comparing phenyl and benzyl groups |
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| the aromatic group that remains after the removal of a hydrogen from an aromatic ring |
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| some physical properties of benzene and its derivatives |
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Definition
| higher boiling points and better able to pack into crystals than similar aliphatic compounds |
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| why benzene has higher boiling point and better crystal packing ability than its aliphatic counterparts |
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Definition
| because it's more symmetrical |
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Term
| how o, m, and p positioning on the benzene ring affect the molecule's boiling point |
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Definition
| positioning affects dipole moment, and dipole moment affects boiling point; the greater the dipole moment, the higher the boiling point |
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