Engineering chemistry Twana Mohammed

Aromatic Compounds

Aromatic Hydrocarbons: Hydrocarbons containing one or more benzene rings

called aromatic hydrocarbons. The word aromatic was derived from (aroma) which
describes the odor of these compounds.

Benzene has the molecular formula C6H6. Benzene was known to contain six carbon
atoms and six hydrogen atoms.

The Resonance Structures of Benzene

 Nomenclature of Benzene Derivatives

Monosubstituted Benzenes
1. When a single hydrogen of the benzene ring is replaced, the compound can be
named as a derivative of benzene.

2. A number of benzene derivatives are known by their common (trivial) names

rather than by their formal IUPAC names.

3. Compounds formed by replacing a hydrogen of benzene with a more complex

hydrocarbon group can be named by naming the benzene ring as the substituent,
called the phenyl group.
B. Disubstituted Benzenes

4. When two groups are attached to a benzene ring, three isomeric structures are
possible:
C. Polysubstituted Benzenes

5. When three or more substituents are present on a ring, their locations are specified
by numerals. If one of the substituents imparts a special name, then the compound
is named as a derivative of that parent molecule. If none of the substituents imparts
a special name, the substituents are numbered to give the smallest set of numbers
and are listed in alphabetical order before the ending -benzene. In the following
examples, the first compound is a derivative of toluene, and the second is a derivative
of phenol. Because there is no special name for the third compound, its three
substituents are listed in alphabetical order, and the atoms of the ring are numbered
using the lowest possible set of numbers.
Exercise: Provide a systematic name for each of the following compounds:

Exercise: For each of the following compounds, draw its structure:

2,6-Dibromo-4-chloroanisole
meta-Nitrophenol
2,4,6-Tribromoaniline
2,6- Dinitrotoluene
3-Bromo-5-nitrotoluene
1-chloro-2, 4-dinitrobenzene
3-nitrotoluene
1, 4-dimethylbenzene
2, 4, 6-trinitrotoluene
3-ethyl-2-methylaniline
1-ethyl-3-nitrobenzene
 Physical Properties of Aromatic Compounds

Just like alkanes and alkenes, aromatic compounds are nonpolar, and therefore
insoluble in water (unless other substituents, such as OH groups, are present). They
are also usually less dense than water.
• Many aromatic compounds are obtained from petroleum and coal tar.
• Benzene and toluene are commonly used as solvents, and are the starting materials
for the synthesis of other useful organic compounds.
• Some foods contain aromatic compounds, which can be synthesized by some
plants. Some aromatic amino acids and vitamins are listed as essential, because we
lack the ability to synthesize them, and must obtain them from our diet.

Reactions of benzene

The most characteristic reaction of aromatic compounds is substitution at a ring

carbon:
1- Halogenation:

2- Nitration:
3- Sulfonation:

4- Friedel–Crafts Alkylation of Benzene

5- Friedel–Crafts Acylation of Benzene