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EAS Lab Manual Not Edited 1

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42 views4 pages

EAS Lab Manual Not Edited 1

Uploaded by

Téo Joca Therrien
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Experiment #7

Electrophilic Aromatic Substitution:


Bromination of Acetanilide

Introduction
Aromatic compounds undergo electrophilic aromatic substitutions in which the
presence and the type of a substituent on the reactant arene have pronounced effect on
the regioselectivity of the substitution. The acetamido group (-NHCOCH 3) in acetanilide
is a strong activating group since the lone pair on the nitrogen of this substituent can be
effectively delocalized into the benzene ring. Hence, the acetamido group generally
directs the substitution to take place either at ortho- and/or para-position.

In this experiment, you will perform bromination of acetanilide, and determine the
identity of a di-substituted bromo-regioisomer produced from the reaction by melting
point. The reaction scheme is shown below in Figure 7.1.

Acetanilide Bromine Possible product


M.P = 114oC B.P = 58.8oC 2-bromoacetanilide (M.P =
99oC) or
d = 3.12 g/mL 3-bromoacetanilde (M.P =
87.5oC) or
4-bromoacetanilde (M.P = 168oC)

SAFETY INFORMATION

 Acetanilide is toxic and an irritant. Avoid contact with skin, eyes and clothing.
 Glacial acetic acid is corrosive and causes burns. Use it in the fume hood and avoid
contact with skin and eyes.
 Bromine is very corrosive and causes serious burns. Use droppers and dispense in
fume hoods only.
 Ethanol is flammable.

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Procedure

1. Place 0.50g of acetanilide into a 10 mL beaker.


2. Add 2.0 mL of glacial acetic acid (colourless solution!) to the beaker.
3. Put the spin vane (stirrer bar) in the beaker.
4. Place the aluminum blocks on the hot plate and have the heat knob off.
5. Place the beaker between the two aluminum blocks and turn the stir knob on and
stir until all the acetanilide is dissolved.
6. Do this step in the fume hood, and avoid breathing the bromine vapours.
Dispense 1.0 mL of 4.1 M bromine in acetic acid solution (brown solution) into a
10 mL cylinder. Add the bromine solution dropwise to the beaker over a two to
three minute period, with continuous swirling. Cover the beaker with some
parafilm. You may now work on your own benchtop.
7. Stir the reaction mixture for 15 minutes with the stir knob on and heat knob off.
8. Pour the reaction mixture into a 50 mL beaker containing 15 mL of water. Rinse
the beaker with 3 mL of water and transfer the rinse into the 50 mL beaker. Do
not transfer the vane. Wash the vane and put aside to eventually return
with the borrowed kit.
9. Filter the solution by suction filtration using a Hirsch funnel (wet the paper in the
funnel with water). Wash the precipitate 4 times with 3 mL portions of cold water.
10. To recrystallize transfer the precipitate (crude product) from the funnel into a 10-
mL beaker.
11. Boil about 10 mL of 80% ethanol in a 50 mL Erlenmeyer flask. Bring the boiling
ethanol to the bench top.
12. Add 5 drops of hot ethanol into the 10 mL beaker containing the crude product
and place the beaker on the hot plate on a low setting.
13. Quickly start adding the hot ethanol dropwise into the beaker on the hot plate
until the entire crude product is dissolved (about 4 mL of hot ethanol is needed).
14. Cool the beaker to room temperature (about 5 minutes).
15. Place some ice-water mixture in a 50 mL beaker and place the 10 mL beaker
with crystals in the ice-bath to cool for 5 minutes.

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16. Filter the solution by suction filtration using a Hirsch funnel (wet the filter paper
with few drops of 80% ethanol).
17. Wash the crystals with ice cold 80% ethanol twice using just enough solvent to
cover the crystals. Continue the suction so that the product dries on the funnel.
18. Remove the crystals from the funnel onto a pre-weighed watch glass and let it
stand for 10 minutes to air dry.
19. Weigh the product.
20. Determine the melting point of the recrystallized product and identify the product.

CLEAN UP

 Pour the aqueous filtrate from the crude product into a large beaker and neutralize
the acid with solid sodium carbonate before pouring the solution down the sink
 Pour the filtrate from the recrystallization step into the organic waste.

36
Name Section

Partner’s Name Date

Experiment 7

Electrophilic Aromatic Substitution: 


Bromination of Acetanilide
DATA SHEET

1. Mass of acetanilide used


_________________________________

2. Moles of acetanilide used


_________________________________
Mass of product obtained after
3. ______________________________
recrystallization

4. Percent yield ______________________________

5. Melting point of the product _________________________________

6. Identification of the product formed _________________________________

Post-Laboratory Questions
1) Show the percent yield calculation.
2) Using curved-arrow notation, draw all possible resonance structures of acetanilide.
3) Provide the structure of the product you obtained from the experiment.
4) This reaction in principle should give two regioisomers; yet, you obtain only one.
Provide a concise explanation to this discrepancy based on the structure of the
substituent.
5) If the starting material was phenol (also known as hydroxybenzene) instead of
acetanilide and an excess of bromine was used, what product(s) would be obtained?
Explain.

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