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Chapter 16: Aromatic Compounds
Chapter 16: Aromatic Compounds
97
Organic Chemistry
Undergraduate 2
09/14/2019

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Term
aliphatic
Definition
fatlike
Term
bond order between adjacent C atoms in a benzene ring
Definition
1 1/2
Term
how the bond lengths between adjacent C's in benzene compare to typical single and double bonds
Definition
shorter than single bonds, but longer than double bonds
Term
benzoid aromatic compounds
Definition
derivatives of benzene
Term
why benzene and other aromatic compounds have unusal reaction properties
Definition
because aromatic compounds are more stable than they would be if stabilized by resonance
Term
illustration of the stability of benzene compared to alkene
Definition
[image]
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Term
bond angles in benzene rings
Definition
120°
Term
how the pi electrons are distributed in a benzene
Definition
all the unhybridized p orbitals align and overlap
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Term
the type of rxn that normally takes place on a benzene ring
Definition
substitution
Term
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Definition
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Term
the product that does not result from this reaction
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Definition
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Term
the molar heat of hydrogenation of benzene compared to that of some other 6-membered rings
Definition
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Term
annulenes
Definition
cyclic hydrocarbons with alternating single and double bonds
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Term
the π molecular orbitals of benzene, viewed from above
Definition
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Term
the π1 energy level of benzene
Definition
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Term
the π2 energy level of benzene
Definition
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Term
the π3 energy level of benzene
Definition
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Term
the π*4 energy level of benzene
Definition
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Term
the π*5 energy level of benzene
Definition
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Term
the π*6 energy level of benzene
Definition
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Term
degenerate
Definition
equal in energy
Term
energy diagram of benzene
Definition
[image]
Term
what the * in π* means
Definition
antibonding π orbital
Term
molecular orbitals or cyclobutadiene
Definition
[image]
Term
energy diagram of cyclobutadiene
Definition
[image]
Term
polygon rule
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
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Term
criteria for a ring to be aromatic
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,...))
Term
antiaromatic
Definition
cyclic, planar, and has unhybridized P orbitals at each ring atom, but wrong number of π electrons
Term
what antiaromaticity does to a ring
Definition
makes it less stable and increases the electron energy
Term
nonaromatic aka aliphatic
Definition
does not have a continuous, overlapping ring of p orbitals
Term
molecular orbitals of aromatic rings compared to those of antiaromatic rings
Definition
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Term
molecular orbitals for 5-membered carbocations and carbanions
Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
heterocyclic compound
Definition
compound that contains a ring of sp2-hybridized atoms other than C, such as O, N, and S
Term
the way electrons are distributed in pyridine
Definition
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Term
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Definition
pyridine
Term
pyridine
Definition
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Term
pyridine acting as a base
Definition
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Term
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Definition
pyrrole
Term
pyrrole
Definition
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Term
how electrons are distributed in pyrrole
Definition
[image]
Term
why pyrrole is a weak base but protonated pyrrole is a strong acid
Definition
because the N becomes sp3-hybridized, thus non-planar, when it abstracts a proton [image]
Term
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Definition
pyrimidine
Term
pyrimidine
Definition
[image]
Term
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Definition
imidazole
Term
imidazole
Definition
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Term
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Definition
purine
Term
purine
Definition
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Term
basic and non-basic N atoms in an aromatic ring
Definition
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Term
imidazole protonating and deprotonating
Definition
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Term
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Definition
cyclopentadienyl anion
Term
cyclopentadienyl anion
Definition
[image]
Term
[image]
Definition
pyrrole
Term
pyrrole
Definition
[image]
Term
[image]
Definition
furan
Term
furan
Definition
[image]
Term
[image]
Definition
thiophene
Term
thiophene
Definition
[image]
Term
how electrons are distributed in some 5-membered heterocycles
Definition
[image]
Term
polynuclear aromatic hydrocarbons
Definition
aromatic compounds composed of 2 or more benzene rings
Term
[image]
Definition
naphthalene
Term
naphthalene
Definition
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Term
what happens when the number of fused benzene rings increases?
Definition
-resonance energy per ring decreases
-compounds become more reactive
Term
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Definition
anthracene
Term
anthracene
Definition
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Term
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Definition
phenanthrene
Term
phenanthrene
Definition
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Term
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Definition
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Term
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Definition
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Term
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Definition
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Term
how benzo[a]pyrene, a polynuclear aromatic hydrocarbon, damages DNA
Definition
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Term
phenyl group
Definition
the benzene ring as a substituent
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Term
[image]
Definition
phenyl group
Term
benzyl group
Definition
the 7-C unit containing the benzene ring and the adjacent methylene
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Term
[image]
Definition
benzyl group
Term
comparing phenyl and benzyl groups
Definition
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Term
arene
Definition
aromatic hydrocarbon
Term
aryl group (Ar)
Definition
the aromatic group that remains after the removal of a hydrogen from an aromatic ring
Term
some physical properties of benzene and its derivatives
Definition
higher boiling points and better able to pack into crystals than similar aliphatic compounds
Term
why benzene has higher boiling point and better crystal packing ability than its aliphatic counterparts
Definition
because it's more symmetrical
Term
how o, m, and p positioning on the benzene ring affect the molecule's boiling point
Definition
positioning affects dipole moment, and dipole moment affects boiling point; the greater the dipole moment, the higher the boiling point
Term
[image]
Definition
aniline
Term
aniline
Definition
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Term
[image]
Definition
anisole
Term
anisole
Definition
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Term
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Definition
benzaldehyde
Term
benzaldehyde
Definition
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Term
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Definition
benzoic acid
Term
benzoic acid
Definition
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Term
[image]
Definition
phenol
Term
phenol
Definition
[image]
Term
[image]
Definition
toluene
Term
toluene
Definition
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