Lecture 2

Aromatic compounds
a) cyclic Extra stability
b) continuous p orbital overlap
c) 4n + 2 delocalised electrons

-Hückel's rules

sp2 sp2

- cyclic
- continuous p orbital overlap
- 4 e- delocalised Extra unstable

4n → Anti-aromatic

sp3

Cycloheptatriene

Aromatic?
a) cyclic
b) 6 e-
c) no continuous p orbital overlap
Not aromatic

CH2 + -

sp sp
3 2
Non-aromatic anti-aromatic aromatic
 -

..
X C C ↔ X C C

sp2

Non-aromatic
-no p orbital overlap
..

..
THF

Non-aromatic
-no p orbital overlap

Dihydrofuran

Linear
180º

sp
furan
 In p orbital
C C
..

O
..

sp2
C C

sp2 sp2 p C C
..
..

sp2 H N
sp2
sp2
C C
Pyrrole

C C

N C
..

..

Pyridine
C C
out on the side
→ in an sp2 orbital
not counted for
aromaticity
Aromatic nomenclature
CH3 OH NH2 COOH

benzene Methylbenzene phenol aminobenzene benzoic Vinyl benzene

or toluene or aniline acid or styrene

Disubstituted benzene

1,2 dichlorobenzene
(o-)
or ortho-dichlorobenzene

(m-)
1,3 dichlorobenzene
(p-) or meta-dichlorobenzene

CH3 Br

paranitrotoluene
Para bromonitrobenzene

NO2 NO2

3 or more substituents

CH3

1
6
2 2, 4, 6 trinitrotoluene

5 3

4
Aromatic reactions
-Electrohilic aromatic substitutions

Br2
FeBr3 Nothing

Lewis acid

What is going on?

+
.. .. Br Br
Br Br -
..

..

.. .. Br Fe Br
FeBr3
Br

Br
-
Br Fe Br
Br
H Br
+
H H

Br

Only product
0%

Aromaticity is important so is favoured

 C C
Br
C C -
Br Br Fe Br

C C Br

C C
Br
+ -
C C Br Br Fe Br

Br
C C