Aromatic Hydrocarbons

Aromatic Hydrocarbon
• In 1825, Michael Faraday isolated a hydrocarbon called benzene,
which consist of six carbon atoms with one hydrogen atom attach to
each carbon.
• Benzene Family or Benzene containing compounds had fragrant
odors, and that is why they are called Aromatic Compounds.
Aromatic Hydrocarbon
Nomenclature of Benzene Derivatives
Nomenclature of Benzene Derivatives
Nomenclature of Benzene Derivatives
Nomenclature of Benzene Derivatives
Nomenclature of Benzene Derivatives
Nomenclature of Benzene Derivatives
Nomenclature of Benzene Derivatives
Preparation of Benzene
• Polymerization of 3 moles of acetylene
• 3 acetylene C 6H6
• Fe as catalyst at 240°C
• Grignard reaction
• C6H5Br + Mg C6H5MgBr C6H6 + Mg(OH)Br : catalyst are dry ether and HOH
respectively
• Heating phenol with zinc dust (reduction)
C6H5OH + Zn C6H6 + ZnO
• Soda Lime Method
C6H5COONa + NaOH Na2CO3 + C6H6 with CaO as Catalyst (NaOH + CaO = Soda lime)
Chemical Properties of Arenes
• Classical tests for unsaturation, such as bromine addition and permanganate oxidation, do not
normally takes place with benzene.
• A reaction of benzene does occur in the presence of a catalyst.
• “Aromaticity” is preserved by a substitution reaction.
• The special stability of benzene and its derivatives is the modern definition of the term
“Aromaticity”
Stability of Benzene
• Evidence of Unusual Stability
Stability of Benzene
• Evidence of Unusual Stability
Chemical Properties of Arenes
• Combustion reaction (complete)
C6H6 + O2 CO2 + H2O

• Reaction with Halogens (Halogenation: Addition Reaction)

Chemical Properties of Arenes
Chemical Properties of Arenes
Halogenation : Electrophilic Substitution
Chemical Properties of Arenes
• Nitration and Sulfonation of Benzene
Chemical Properties of Arenes
• Friedel-Crafts Alkylation and Acylation of Benzene
Physical Properties of Benzene
• Colorless liquid which is insoluble in water, but soluble in non-polar
organic solvents.
• Density = 0.9841
• Boiling point = 80.08 ◦C
• Melting point = 5.4 ◦C
• Cooling benzene yields hexagonal crystals
Chemical Properties of Benzene Derivatives
• Substitution: An early observations in the studies of aromatic
substitution was that a substituent already on the aromatic ring
directs the position of the subsequent substitution
Chemical Properties of Benzene Derivatives
Chemical Properties of Benzene Derivatives
Chemical Properties of Benzene Derivatives
Oxidation of Benzene Products