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Arenes
2012 C1 Chemistry
Lecture 1
Introduction
What are arenes?
Hydrocarbons that contain one or more
benzene rings
What does the term aromatic mean?
Aromatic compounds refer to benzene and
other compounds stabilized by a ring system
of delocalized electrons
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Independent Learning ubtopic
5 Things about benzene:
C
!
H
!
Planar molecule
"ach C atom is sp
2
hybridised
! unhybridised p orbitals o#erlap to form a
delocalised electron cloud abo#e and belo$
plane of the ring
%elocalised electron cloud confers e&tra
stability onto benzene
Pg '(!
)omenclature
*hen is benzene the +parent, chain-
..benzene
*hen is benzene the +substituent,-
phenyl ..
)ote the traditional names of common compounds
containing benzene/ 0e/g/ phenol1 benzaldehyde1 benzoic acid2
If you ha#e more than one substituent on the benzene
ring1
principal functional group at position 1
achie#e lo$est numbers
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)omenclature
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5eactions of 6enzene
Electrophilic Substitution
Why Electrophilic?
5ich source of electrons abo#e and belo$ the
plane of the ring
Why Substitution?
%elocalized electron cloud confers e&tra
stability
Loss of aromaticity energetically unfa#orable
6enzene does not undergo addition reactions
0unli7e al7enes2
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"lectrophilic ubstitution
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8o preser#e the stable delocalized system9
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"lectrophilic ubstitution9 )itration
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"lectrophilic ubstitution9 )itration
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"nergy profile diagram9
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"lectrophilic ubstitution
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hape and hybridization changes in the
mechanism
"lectrophilic ubstitution
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"lectrophilic ubstitution9 Halogenation
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Le$is acid catalysts9 ;e6r
'
1 Al6r
'
"lectron pair acceptors
<enerate stronger electrophile 6r
=
Can add iron filings instead of ;e6r
'
to generate catalyst ;e6r
'
in
situ9 2;e0s2 = '6r
2
0l2 2;e6r
'
0s2
Chlorination9 Cl
2
1 ;eCl
'
0or AlCl
'
21 $arm
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