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39 Cards in this Set

  • Front
  • Back
Define aromatic
any unusually stable ring system
Aromatic compounds are cyclic....
conjugated, possess 4n+2 electrons, planar
Why do aromatic compounds adopt planar conformation?
to allow maximum overlap of their conjugated pi orbitals
t or f
neutral compounds, anions, and cations all may be aromatic
t
aliphatic (define)
any compound that is not aromatic
Define antiaromatic
Cyclic, conjugated polyenes that are destabilized
Aromatic compounds can also be referred to as..
aryl or arenes
When named as a subsituent benzene is represented by..
Ph
Aliphatic compounds are called ____ and are represented by __.
Aliphatic compounds are called alkyl and represented by the symbol R
1,2 disubstituted compound is called?
ortho
1,3 disubstituted compounds are called
meta-
1,4 disubstituted compounds are called
para-
Name 4 polycyclic (multiple connected) or heterocyclic rings.
napthalene
anthracene
pyrimidine
pyrrole
Pyridines ____ can function as a ____ and pull a ____ out of solution
lone pair, base, proton

**Pyrroles lone pair cannot
t or f
pyrroles lone pair will react
f
The characteristic planar shape of benzene permits the rings six pi orbitals to
overlap, delocalizing the electron density
All 6 carbon atoms are ___ hybridized
sp2
Delocalization stabilizes the molecule, making it
fairly unreactive
Benzene doesnt undergo ___ reactions, but it will undergo ___ reactions
addition, substitution
With benzene, a substitution reaction means...
a hydrogen atom on the ring is replaced by another group
Most common examples to EAS are:
halogenation, sulfonation, nitration, aklylation, and acylation
Aromatic rings react with ___ in the presence of a ___ to yield ____.
Br or Cl, lewis acid, monosub. products
Why are halogenation reactions with F and I less useful?
F- highly reactive, produce multisubstituted products
I- lacks reactivity, requires special conditions
In sulfonation what do the aromatic rings react with?
Sulfuric acid, sulfur trioxide, and head
Product of sulfonation?
Sulfonic acids
Is sulfonation reversible?
yes
What is a nitronium ion?
NO2+ (strong electrophile)
How do you produce nitro compounds?
Nitronium with aromatic ring
For nitration the product of this reaction is the ____ reactive substituted compound b/c it is ____ reactive
least, least
Describe Friedel-Crafts acylation
An acyl group is turned into a carbocation by a Lewis acid, the carbocation acyl group is then incorporated into aromatic ring
Substitution groups are groups according to whether they ____ or ____ substitution
enhance or inhibit
Define activators
groups that donate electron density
Define deactivators
groups that withdraw electron density
Activators direct new substituents to
o/p positions
Deactivators direct new substituents to
meta positions
Halogens are ____ and direct to the ___ position
mild deactivators, o/p position
Benzene rings can be reduced to ____ by ____.
cyclohexane, catalytic hydrogenation
Benzene reduction catalysts include:
Ruthenium or rhodium
Platinum or palladium (higher pressure required)

**elevated temp. and pressure
Aromatic compounds are particularly _____.
Stable