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3. 2. 0. -. Benzene C 6 H 6. Table of Contents. Stats Structure Bonding Electronic Properties Reactions Nomenclature Industry Harmful Effects. Statistics. Discovered by Michael Faraday - 1825 Most Basic Aromatic Molecule Colorless Liquid Boiling Point: 80.08 o C - PowerPoint PPT Presentation
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23 April 2001 Miles Selvidge 1
Benzene CBenzene C66HH66
02
-
3
23 April 2001 Miles Selvidge 2
Table of ContentsTable of Contents
StatsStats StructureStructure BondingBonding Electronic Electronic
PropertiesProperties ReactionsReactions NomenclatureNomenclature IndustryIndustry Harmful EffectsHarmful Effects
23 April 2001 Miles Selvidge 3
StatisticsStatistics
Discovered by Discovered by Michael Faraday - Michael Faraday - 18251825
Most Basic Aromatic Most Basic Aromatic MoleculeMolecule
Colorless LiquidColorless Liquid Boiling Point: Boiling Point:
80.0880.08ooCC Melting Point: 5.48Melting Point: 5.48ooCC Density: .880 g/cmDensity: .880 g/cm33
23 April 2001 Miles Selvidge 4
Statistics Statistics -- continuedcontinued
Insoluble in WaterInsoluble in Water Soluble in Oils & Soluble in Oils &
FatsFats Explosive VaporsExplosive Vapors Flammable LiquidFlammable Liquid
23 April 2001 Miles Selvidge 5
StructureStructure
Flat StructureFlat Structure
Carbon Atoms are Carbon Atoms are
spsp2 2 HybridizedHybridized
Carbon has Carbon has
Triangular Planar Triangular Planar
GeometryGeometry
23 April 2001 Miles Selvidge 6
BondingBonding
Sigma and pi Sigma and pi Bonding between Bonding between Carbon atomsCarbon atoms
Has Resonance Has Resonance Structure ==>Structure ==>
Actual Bonds are Actual Bonds are All Intermediate All Intermediate LengthLength
Increased StabilityIncreased Stability
23 April 2001 Miles Selvidge 7
Electronic PropertiesElectronic Properties
The Six Electrons in the The Six Electrons in the pipi Bonds are Loosely Bonds are Loosely Held Compared to the Held Compared to the Electrons in the Electrons in the sigmasigma BondsBonds
Those Six Electrons are Those Six Electrons are DelocalizedDelocalized• This causes a cloud This causes a cloud
of electrons above of electrons above and below the plane and below the plane of the benzene of the benzene moleculemolecule
23 April 2001 Miles Selvidge 8
ReactionsReactions
The Resonance Structures of Benzene The Resonance Structures of Benzene Increase its StabilityIncrease its Stability• Resist Addition Reactions Because That Resist Addition Reactions Because That
Would Destroy the Ring StructureWould Destroy the Ring Structure• Often Undergoes Substitution ReactionsOften Undergoes Substitution Reactions
Benzene Serves as a Source of Benzene Serves as a Source of Electrons for Electrophilic ReagentsElectrons for Electrophilic Reagents
23 April 2001 Miles Selvidge 9
Reactions Reactions - Types of - Types of SubstitutionsSubstitutions
Nitration:Nitration: C C66HH66 + HNO + HNO33 C C66HH66NONO22 + H + H22OO
Halogenation:Halogenation: Carbon Replaced by Halogen Carbon Replaced by Halogen
Sulfonation:Sulfonation: Carbon Replaced by Sulfer Carbon Replaced by Sulfer
Friedel-crafts:Friedel-crafts: Acyl group (RCO-) Attaches to Acyl group (RCO-) Attaches to
Ring to Make a KeytoneRing to Make a Keytone
Nitrobenzene
23 April 2001 Miles Selvidge 10
Nomenclature of BenzeneNomenclature of Benzene
When Substituent When Substituent Takes its Place in Takes its Place in the Ring the New the Ring the New Molecule’s name Molecule’s name is the is the prefixprefix - -benzenebenzene
Ex: Ex: ChlorobenzeneChlorobenzene
23 April 2001 Miles Selvidge 11
NomenclatureNomenclature - Continued- Continued
If More Than One Group Attaches If More Than One Group Attaches to Benzene then Positions Must be to Benzene then Positions Must be IndicatedIndicated
Ortho (Ortho () = One Space) = One Space
Meta (m) = Two SpacesMeta (m) = Two Spaces
Para (p) = Three SpacesPara (p) = Three Spaces
CH3NO2
NO2
Cl
I
Br
-Nitrotoluene
M-Chloronitrobenzene
p-Bromoiodobenzene
23 April 2001 Miles Selvidge 12
Nomenclature Nomenclature - continued- continued
-Nitrotoluene -Nitrotoluene
m-Chloronitrobenzenem-Chloronitrobenzene
p-Bromoiodobenzenep-Bromoiodobenzene
23 April 2001 Miles Selvidge 13
Nomenclature Nomenclature - continued- continued
If 3 or More Groups AttachIf 3 or More Groups Attach• Numbers are Used to Indicate Numbers are Used to Indicate
PositionsPositions
• 2-Chloro-4-nitrophenol2-Chloro-4-nitrophenolOH
Cl
NO2
12
34
5
6
23 April 2001 Miles Selvidge 14
IndustryIndustry
Made from Coal Tar (a liquid left over Made from Coal Tar (a liquid left over
when coal is heated) and Petroleumwhen coal is heated) and Petroleum
Used as a Source for Almost all Used as a Source for Almost all
Aromatic CompoundsAromatic Compounds• Make Complicated Aromatic Compounds Make Complicated Aromatic Compounds
by Taking Benzene and Add on Other by Taking Benzene and Add on Other Rings Piece by PieceRings Piece by Piece
23 April 2001 Miles Selvidge 15
Industry Industry - continued- continued
Solvent for:Solvent for:
• Sulfur, Phosphorus and IodineSulfur, Phosphorus and Iodine
• GumsGums
• Fats, Waxes and ResinsFats, Waxes and Resins
• Simple Organic CompoundsSimple Organic Compounds– One of the Most Commonly Used Solvents in Organic One of the Most Commonly Used Solvents in Organic
ChemistryChemistry
23 April 2001 Miles Selvidge 16
Industry Industry - continued- continued
Aniline: Aniline: • Dye (Aniline Oil)Dye (Aniline Oil)• PlasticsPlastics• Drugs Drugs
(Sulfanilamide) (Sulfanilamide) • ExplosivesExplosives
Phenol:Phenol:• DisinfectantDisinfectant• Antiseptic (Diluted)Antiseptic (Diluted)• InsecticideInsecticide• ExplosivesExplosives• DetergentDetergent• Raw Material for AspirinRaw Material for Aspirin
Can Make Aniline and PhenolCan Make Aniline and Phenol
23 April 2001 Miles Selvidge 17
Industry Industry - continued- continued
Makes Toluene, a component of Makes Toluene, a component of TNT (Trinitrotoluene)TNT (Trinitrotoluene)
Makes Tear GasMakes Tear Gas
Makes AcetoneMakes Acetone
23 April 2001 Miles Selvidge 18
Toxic NatureToxic Nature
Carcinogen -- Causes LeukemiaCarcinogen -- Causes Leukemia Makes DioxinsMakes Dioxins
• Two Phenols Combine and Cl Connects Two Phenols Combine and Cl Connects to Make Chlorinated Dibenzo-p-dioxinto Make Chlorinated Dibenzo-p-dioxin
Does not Dissolve in Water, but does Does not Dissolve in Water, but does in Oils and Fatsin Oils and Fats• Accumulates in the Food WebAccumulates in the Food Web
Mimics HormonesMimics Hormones• Disrupts Normal Functions and GrowthDisrupts Normal Functions and Growth