1. Structural Properties:
What do aspirin, Tylenol, ibuprofen, almonds, vanilla, and mothballs have in common?
aspirin
Tylenol
ibuprofen
almonds
vanilla
mothballs
Structural Properties:
Planar
All C atoms sp2 hybridized
All C-C bonds equal length
Aromatic ring
 electrons “smeared out”
Resonance structures

2. Structure of Benzene H H C C
Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

3. Benzene 3-D VSEPR Diagram
Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 212

4. Special Stability (aromaticity)
Aromatic Compounds
Benzene, C6H6
Toluene
Phenol
Chemical Properties
Special Stability (aromaticity)
No addition reactions
Hf
Aniline
-156 kJ/mol
Aromatic substituents:
+ 118 kJ/mol
-38 kJ/mol
phenyl
+ 113 kJ/mol
75 kJ/mol
- 26 kJ/mol
benzyl
49 kJ/mol

5. Benzene
C6H6
Uses: styrene; phenol; synthetic detergents; cyclohexane for nylon; DDT; insecticides; fumigants; solvent; paint removers; rubber cement; antiknock gasoline

6. Names of monosubstituted benzene rings
Chlorobenzene
Toluene
Bromobenzene
Phenol
Nitrobenzene
Styrene

7. Phenol, (carbolic acid)
C6H5OH
Uses: solvent for refining lubricating oils; salicylic acid; phenoltpthalein; germicidal paints; pharmaceuticals; laboratory reagent; slimicide
Derivative: ~75% of the phenol produced in the United States is made by the oxidation of cumene, yielding acetone as a by-product.

8. Benzene NO3- Nitrobenzene
Using Computational Chemistry to Explore Concepts in General Chemistry
Mark Wirtz, Edward Ehrat, David L. Cedeno*
Department of Chemistry, Illinois State University, Box 4160, Normal, IL
Mark Wirtz, Edward Ehrat, David L. Cedeno*

9. Aromatic Hydrocarbons
Kelter, Carr, Scott, Chemistry A World of Choices 1999, page 430

10. Cholesterol Compounds

11. CH3 C C C C ortho C C para meta position number name 1, 2 ortho- (o-)6 C C 1 C C
ortho 5 2 C C 3 4
para
meta
position number name
1, 2 ortho- (o-)
1,3 meta- (m-)
1,4 para- (p-)

12. ortho-dimethylbenzeneC H
CH3 6 1 5 2 3 4
ortho-dimethylbenzene or
1, 2 - dimethylbenzene

13. meta-dimethylbenzeneC H
CH3 6 1 5 2 3 4
meta-dimethylbenzene or
1, 3 - dimethylbenzene

14. para-dimethylbenzeneC H
CH3 6 1 5 2 3 4
para-dimethylbenzene or
1, 4 - dimethylbenzene

15. C H MD 6 1 5 2 3 4
para-docs or
paradox

16. C H MD 6 1 5 2 3 4
ortho-docs or
orthodox

17. C
Fe2+ 6 1 5 2 3 4
ferrous wheel or
ferris wheel

18. C H
NO2
o - dinitrobenzene or
1, 2 - dinitrobenzene

19. C
CH3
NO2 H
O2N
Toluene
2,4,6 - trinitrotoluene or
TNT

20. 2,4,6 -Trinitrotoluene CH3C6H2(NO2) 3
Uses: Explosives; intermediate in dyestuffs and photographic chemicals
Will detonate only if vigorously shocked or heated to 450oF

21. 2, 4, 6 -trichloromethylbenzeneCl
CH3 H
Toluene
2, 4, 6 - trichlorotoluene or
2, 4, 6 -trichloromethylbenzene

22. O H O C CH3 C C H C C COOH C C H H 2-acetyloxybenzoic acid or
(acetylsalicylic acid or aspirin)

23. dichlorodiphenyltrichloroethaneCl C C C C C Cl Cl C
CCl3 C C C C H H H H
dichlorodiphenyltrichloroethane or
DDT

24. H CH CH2 C C H C C H C C H H phenyl ethene or styrene poly
a.k.a. (styrofoam)