Lecture 1

Aromatic chemistry
Hybridisation

CH3 – CH2 – O – CH2 – CH3

..
..
sp3 sp3 sp3
sp3
s sp3 s

-Hybrid orbitals
H 1s1 → always an s orbital

C 2s 2px 2py 2pz

(along the z axis)

4 equal bonds

(s, p, p) p
remains in bonding

Used in π bond

σ
π → p orbital
 sp2 bonds are trigonal planar

CH3 – C ≡ N

sp

C N linear

Resonance

- sp2

Therefore, both Os are sp2

+
sp2

.. ..
X C Y ↔ X C Y

must be in a p orbital
Aromatic chemistry - shells

TNT – Trinitrotoluene

0 double bonds → sp3

1 double bond → sp2
2 double bonds/triple bond → sp1

CH3 – C ≡ C – CH2 – OH

sp3 sp sp sp2 sp3

+
H2C – R → positive charge is in a p orbital

sp2

H
+
C R Flat – trigonal planar

Resonance sp2

O
..
CH3 – C – O
.. – CH2 – CH3
sp3 sp2 sp3
 sp2

all sp2

sp2

-Flat
-All bond lengths are 1.5 Å

The delocalisation translates to:

-lower reactivity compared to alkenes
-shorter bond length
-stability

How can we tell if a compound is aromatic?

a) Flat
b) continuous p orbital overlap
c) 4n + 2 electrons in delocalised cloud → Hückel's rules

4 π electrons
↓
aromatic