What do aspirin, Tylenol, ibuprofen, almonds, vanilla, and mothballs have in common?

1

• 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
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
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
Nitrobenzene
Phenol
Styrene
7
Phenol, (carbolic acid)

• C6H5OH
• Uses solvent for refining lubricating oils
  salicylic acid phenoltpthalein germicidal
  paints pharmaceuticals laboratory reagent
  slimicide

8
Benzene
NO3-
Nitrobenzene
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
6
C
C
1
ortho
C
C
2
5
C
C
3
4
meta
para
position number name 1, 2 ortho-
(o-) 1,3 meta- (m-) 1,4 para-
(p-)
12
6
1
2
5
3
4
ortho-dimethylbenzene or 1, 2 - dimethylbenzene
13
6
1
2
5
3
4
meta-dimethylbenzene or 1, 3 - dimethylbenzene
14
6
1
2
5
3
4
para-dimethylbenzene or 1, 4 - dimethylbenzene
15
6
1
2
5
3
4
para-docs or paradox
16
6
1
2
5
3
4
ortho-docs or orthodox
17
6
1
2
5
3
4
ferrous wheel or ferris wheel
18
o - dinitrobenzene or 1, 2 - dinitrobenzene
19
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
Toluene
2, 4, 6 - trichlorotoluene or 2, 4, 6
-trichloromethylbenzene
22
O
O
C
CH3
H
C
C
H
COOH
C
C
C
C
H
H
2-acetyloxybenzoic acid or (acetylsalicylic acid
or aspirin)
23
H
H
H
H
C
C
C
C
H
Cl
C
C
C
C
C
Cl
CCl3
C
C
C
C
C
H
H
H
H
dichlorodiphenyltrichloroethane or DDT
24
CH
CH2
H
C
C
H
H
C
C
C
C
H
H
n
phenyl ethene or styrene
a.k.a. (styrofoam)
poly