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Electrophilic Aromatic Substitution

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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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