Electrophilic Aromatic Substitution
Essay by betkah • December 5, 2015 • Lab Report • 530 Words (3 Pages) • 1,829 Views
Experiment 5. Electrophilic Aromatic Substitution
Objective:
To determine whether a series of different aromatic compound would react with bromine, and if so how long would it take for the aromatic compound to react to it.
Equation:
Reference:
P.Marrs, Chemistry 232 Lab Manual, pp. A-53-A-64. (University of Victoria: Victoria, BC). Spring 2013.1
Reagents and Products Data Table:
Compound
MW(g/mol)
Used
Moles
Physical/Safety Data
Benzene
C6H6
78.11
3.0mL
0.033
Bp 80oC, mp 5.5oC. d 0.874g/mL. Flammable liquid, Irritant, health hazard
Nitrobenzene
C6H5NO2
123.11
3.0mL
0.0291
Bp 210-211oC, mp 5-6oC. D 1.196g/mL at 25oC.Toxic,health hazard,hazardous to environment.
Chlorobenzene,C6H5Cl
112.56
3.0mL
0.0294
Bp 132oC, mp -45oC. D 1.106 g/mL at 25oC.Flammable liquid, toxic, irritant hazardous to environment.
Acetanilide CH3CONHC6H5
135.16
3.0mL
0.0270
Bp 304oC mp 113-113oC. d 1.22g/mL.Toxic and Irritant
Anisole CH3OC6H5
108.14
3.0mL
0.0276
Bp 154oC, mp -37oC. D 0.995 g/mL at 25oC. Flammable liquid, toxic, Irritant.
Bromine,Br2
159.82
27mL
0.527
Mp – 7.3oC, bp 59.5oC d 3.12g/mL. Volatile,highly toxic,oxidizer,corrosive.Dispose of test solution as directed.
Acetic acid CH3CO2H
60.05
6.0mL
0.104
Bp 117-118oC.mp 16.2oC. D 1.049 g/mL at 25oC. Flammable liquid, corrosive to skin.
0.5M diphenyl ether (C6H5)2O
170.21
9.0mL
0.0056
Bp 259 oC. Mp 25-27oC. D 1.073 g/mL at 25oC. Corrosive to skin.
Phenol
94.11
3.0mL
0.0034
Bp 182oC mp 40-42oC. d 1.071 g/mL. Corrosive, toxic. Health hazard.
Table 2. Deactivated Aromatic Compound absorbance readings:
Compound
45 mins
50 mins
55 mins
60 mins
Benzene
.862
.754
.678
.597
Chlorobenzene
.842
.758
.687
.600
Nitrobenzene
.466
.778
.706
.649
Table 3. Activated Aromatic Compound rate of bromination:
Time of Mix
Time of Dissappearance
Bromine color
Phenol
0.00
<0.06s
colorless
Diphenyl ether
0.00
<7.32s
Pale yellow
p-bromophenol
0.00
0.26s
Color-less
Acetanilide
0.00
<4.29s
clear
Anisole
0.00
1.08s
Colorless
Table 4. Rate of bromination In Room Temperate @ 21oC
Compound
Time of Disappearance
Bromine appearance
Diphenyl ether
<3.34s
Pale yellow
p-bromophenol
0.10s
Colorless
Acetanilide
0.21s
Clear
Anisole
0.11s
colorless
Table 5. Rate of Bromination of Diphenyl ether @ 50oC
Compound
Time of Dissappearance
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