MOD 9 Flashcards
chemical formula of BENZENE
C6H6
Chemical reactivity of BENZENE
electrophilic substitution
the EXTRA STABILITY associated with aromatic compounds.
AROMATICITY
contain elements other than carbon in a ring, such as N,S,O,P.
Heterocyclic compounds
can have elements other than carbon in the ring.
Aromatic compounds
Cyclic compounds that contain only carbon are called
carbocycles
A SIX-membered heterocycle with a NITROGEN atom in its ring
PYRIDINE
Pyridine is a ____________ compared to normal
amines but protonation does not affect aromaticity
RELATIVELY WEAK BASE
A FIVE-membered heterocycle with ONE NITROGEN
PYRROLE
Since lone pair electrons are in the
aromatic ring, protonation destroys
aromaticity, making pyrrole a ____________
VERY WEAK BASE
Cl2 and Br2 are weak electrophiles on their own so need to be “activated” by using a
LEWIS ACID CATALYST
In the case of nitration, _________ is used to generate a more reactivity electrophile, a nitronium ion.
SULFURIC ACID
a more reactivity electrophile
NITRONIUM ION
______ will generate a benzenesulfonic acid.
SULFONATION
the strong electrophile that Sulfonation uses
SULFUR TRIOXIDE
_________ will add an alkane group to benzene
ALKYLATION
In alkylation, the electrophile used is
CARBOCATION
This process uses an ALKYL HALIDE (Cl or Br usually) and a LEWIS ACID CATALYST similar to a halogenation reaction.
Friedel-Crafts Alkylation
Friedel-Crafts Alkylation product
alkylbenzene
Alkylation from Alkenes
PHENYL KETONE
Alkylation can also be achieved by using an ALKENE and an ACID (sulfuric as the conjugate base is a poor nucleophile)
ALKYLATION FROM ALKENES
Alkylation from Alkenes will generate _________
MARKOVNIKOV CARBOCATION
