Introduction to Organic Chemistry

No. of steroisomers = 2n
n = number of sterocentres
(double-bonds & chiral centres)

Hybridisation – mixing orbitals

sp3 : 1 of the 2s electrons in C is promoted to the vacant 2p orbital. The s

and p orbitals hybridise to give 4 identical sp3 hybrid orbitals of equal energy.

sp2: 1 of the 2s electrons in C is promoted to the vacant 2p orbital. s orbital

hybridise with two p orbitals to give 3 identical sp2 hybrid orbitals.

sp: 1 of the 2s electrons in C is promoted to the vacant 2p orbital. s orbital

hybridise with px orbital to give 2 identical sp hybrid orbitals.

Sigma (σ) bond and pi (π) bond

σ bonds are formed by head-on overlap of any 2 orbitals.

When a σ bond is formed, it may bring two parallel p orbitals into close proximity. Side-on overlap
of the p orbitals forms a π bond.

The C=C double bond in ethene consists of 1 σ and 1 π bond.

The C≡C triple bond in ethyne consists of 1 σ and 2 π bond.

Note: A π bond can only form after a σ bond has already formed. It is always part of a double or
triple bond.

Homolytic fission:

Heterolytic fission:
Reaction Mechanisms

Free Radical Substitution Electrophilic Addition

(1) Initiation:

(2) Propagation:

(3) Termination:

Electrophilic Substitution (Nitration) Electrophilic Substitution (Halogenation)

Nucleophilic Substitution

Nucleophilic Addition