Benzene C 6H 6

2 0
-

23 April 2001 Miles Selvidge 1

 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
Molecule’s 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
CH3
 Ortho () = One Space
-Nitrotoluene
NO2

NO2
 Meta (m) = Two Spaces
M-Chloronitrobenzene Cl
 Para (p) = Three Spaces I

p-Bromoiodobenzene
Br
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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
1
6 2 Cl
5 3
4

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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:
 Phenol:
• Disinfectant
• Dye (Aniline Oil)
• Antiseptic (Diluted)
• Plastics
• Insecticide
• Drugs (Sulfanilamide) • Explosives
• 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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