Benzene

C 6H 6
3
2

0
-

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Miles Selvidge

Table of Contents

Stats
Structure
Bonding
Electronic Properties
Reactions
Nomenclature
Industry
Harmful Effects

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Statistics

Discovered by Michael
Faraday - 1825
Most Basic Aromatic
Molecule
Colorless Liquid
Boiling Point: 80.08oC
Melting Point: 5.48oC
Density: .880 g/cm3

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Statistics - continued

Insoluble in Water
Soluble in Oils & Fats
Explosive Vapors
Flammable Liquid

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Structure

Flat Structure

Carbon Atoms are sp2

Hybridized

Carbon has Triangular

Planar Geometry

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Bonding

Sigma and pi Bonding

between Carbon
atoms
Has Resonance
Structure ==>
Actual Bonds are All
Intermediate Length
Increased Stability

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Electronic Properties

The Six Electrons in the pi

Bonds are Loosely Held
Compared to the Electrons
in the sigma Bonds
Those Six Electrons are
Delocalized
This causes a cloud of
electrons above and
below the plane of the
benzene molecule

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Reactions

The Resonance Structures of Benzene

Increase its Stability
Resist Addition Reactions Because That Would
Destroy the Ring Structure
Often Undergoes Substitution Reactions

Benzene Serves as a Source of Electrons for

Electrophilic Reagents

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Reactions - Types of Substitutions

Nitration: C6H6 + HNO3

C6H6NO2 + H2O
Nitrobenzene

Halogenation: Carbon Replaced by Halogen

Sulfonation: Carbon Replaced by Sulfer

Friedel-crafts: Acyl group (RCO-) Attaches to

Ring to Make a Keytone

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Nomenclature of Benzene

When Substituent
Takes its Place in the
Ring the New
Molecules name is
the prefix -benzene

Ex: Chlorobenzene

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Nomenclature - Continued

If More Than One Group Attaches to

Benzene then Positions Must be Indicated
Ortho () = One Space
-Nitrotoluene

CH3

NO2
NO2

Meta (m) = Two Spaces

M-Chloronitrobenzene
I

Cl

Para (p) = Three Spaces

p-Bromoiodobenzene

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Br

11

Nomenclature - continued

-Nitrotoluene

m-Chloronitrobenzene

p-Bromoiodobenzene

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Nomenclature - continued

If 3 or More Groups Attach

Numbers are Used to Indicate Positions
2-Chloro-4-nitrophenol
OH
6

Cl

3
4

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NO2

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Industry

Made from Coal Tar (a liquid left over when

coal is heated) and Petroleum

Used as a Source for Almost all Aromatic

Compounds
Make Complicated Aromatic Compounds by
Taking Benzene and Add on Other Rings Piece
by Piece

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Industry - continued

Solvent for:
Sulfur, Phosphorus and Iodine
Gums
Fats, Waxes and Resins
Simple Organic Compounds
One of the Most Commonly Used Solvents in Organic Chemistry

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Industry - continued
Can Make Aniline and Phenol

Aniline:

Dye (Aniline Oil)

Plastics
Drugs (Sulfanilamide)
Explosives

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Phenol:

Disinfectant
Antiseptic (Diluted)
Insecticide
Explosives
Detergent
Raw Material for Aspirin

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Industry - continued

Makes Toluene, a component of TNT

(Trinitrotoluene)

Makes Tear Gas

Makes Acetone

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Toxic Nature
Carcinogen -- Causes Leukemia
Makes Dioxins

Two Phenols Combine and Cl Connects to Make

Chlorinated Dibenzo-p-dioxin

Does not Dissolve in Water, but does in Oils

and Fats
Accumulates in the Food Web

Mimics Hormones
Disrupts Normal Functions and Growth

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