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29 Cards in this Set

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aromatic
unusually stable ring systems made up of cyclic, conjugated polyenes with 4n+2 pi electrons and a planar conformation allowing for maximum overlap of conjugated pi orbitals
alphiatic
all compounds that are not aromatic
Huckel's Rule
4n+2 pi electrons in an aromatic compound. Important indicator of aromaticity.
anti-aromatic
a cyclic, conjugated polyene with 4n electrons
destabilized
nomenclature
aromatics are called aryl compounds or arenes (Ar)

aliphatic are called alkyl (R)
toluene
benzene with 1 methyl sub
phenol
benzene with 1 hydroxyl sub
aniline
benzene with 1 amine sub
anisole
benzene with 1 OCH3 sub. (ether)
phenyl group (Ph)
benzene named as a sub
benzyl
toluene molecules as a sub

example:
benzyl chloride
ortho (o)
1,2 disub'ed benzene
meta (m)
1,3 disub'ed benzene
para (p)
1,4 disub'ed benzene
naphthalene
10 membered aromatic double ring, looks like two benzenes stuck to each other
anthracene
three ring aromatic compound, looks like three benzenes stuck end-to-end
pyridine
benzene with one C replaced with a N
pyrrole
5 membered aromatic ring, has 4 C and 1 NH
physical properties
generally similar to other hydrocarbons
chemical properties
pi system causes electron density delocalization

all C are sp2

stable, fairly unreactive
electrophilic aromatic substitution
an electrophile replaces a proton on an aromatic ring
halogenation
Ar + X2 +FeX2 + heat = ArX

X=Br or Cl
F and I are not useful
Fe can also be Al
Sulfonation
Ar + SO3/H2SO4 + heat = ArSO3H

forms sulfonic acids
nitration
Ar + H2SO4 + HNO3 = ArNO2

attaches a nitro group
Friedel-Crafts acylation
Ar + CH3COCl + AlCl3 = ArCOCH3 + HCl

attaches an acyl group

also works for alkylation
activating substituents, o/p directing
NH2, NR2, OH, NHCOR, OR, OCOR, R
deactivating substituents, o/p directing
F, Cl, Br, I
deactivating substituents, meta directing
NO2, SO3H, carbonyl compounds including COOH, COOR, COR, and CHO
catalytic reduction
convert benzene to cyclohexane

H2, Ruthenium or Rhodium, 100 degrees C

platinum or palladium may also be used