Synthesis of Acetanilide

Objective: To synthesize acetanilide in a reaction between aniline and acetic anhydride.

Materials Used:
Name Formula Molecular weight Density Boiling Point Melting Point

Acetic acid CH COOH

3 60.05 g/mol 1.05 g/cm³ 118.1°C 16.6°C

Acetic anhydride C H O
4 6 3 102.09 g/mol 1.08 g/cm³ 139.8°C -73.1°C

Aniline C H NH
6 5 2 93.13 g/mol 184.1°C -6.3°C
1.02 g/cm³

Acetanilide C H NO
8 9 135.17g/mol 1.22g/cm³ 304°C 114.3°C

Water HO2 18.015 g/mol 1 g/cm³ 100°C 0°C

Procedure:
1. Place 10ml of glacial acetic acid and 2.0ml (d=1.08g; 2.2g) of acetic anhydride in a 50ml
round bottomed flask. Add dropwise 2.2ml (d=1.02g/ml ; 2.2g) of aniline and reflux for 1
hour.
2. Pour the hot contents of the reaction flask into a beaker containing 50ml of cold water
and stir vigorously.
3. Filter with suction and wash the crystals with about 5ml of ice cold water.
4. Transfer the crystals to another beaker containing 60ml of water and heat to dissolve the
acetanilide.
5. If the solution is colored, add a pinch of charcoal and heat to boiling. Filter with suction
while it is still hot and cool the filtrate to room temp.
6. Immerse the mixture in an ice water bath and let it stand for 5-10mins.
7. Collect the crystals by vacuum filtration through a buchner funnel and air dry.
8. Determine the MP and percent yield.

Results:
Aniline= 0.024 mole
M=DV MASS= 2.2ml x 1.02g/mol = 2.2g
Mole= mass/Molecular weight = 2.2g / 93.13g/mole = 0.024mole

Acetic Anhydride= 0.021 mole

Mass= 2.0ml x 1.08g/mol = 2.16g
Mole = 2.16g / 102.09g/mol = 0.021mole

Limiting reagent= Acetic Anhydride because mole of acetic anhydride is less than aniline.
Product: Acetanilide = 0.013 mole
M=1.77g
Mole= 1.77g / 135.17g/mol = 0.013mol

Theoretical Yield =0.021

Actual Yield = 0.013

% Yield = 61.9%
0.013mole of acetanilide / 0.021 mole of acetic anhydride = .619 x 100
Discussion:
In this experiment, we synthesized acetanilide from aniline and acetic anhydride by mixing 10ml
of acetic acid, 2.0ml is acetic anhydride and 2.2ml of aniline and mixed it all together and reflux
for an hour. After an hour, we took the content in the reaction flask and stirred in cold water
which produced a thick peachy brown color. We then took the mixture and set up vacuum
filtration to filter the crystals. After vacuum filtration, we transferred the crystals to a 250ml
Erlenmeyer flask with some water and heated it which dissolved the acetanilide. Charcoal was
also mixed in so that the impurities will filter out when it attaches itself to the carbon. We then
filtered out the charcoal and took the flask of the product and cooled it to room temperature.
While waiting, the surface of the flask was scratched to produce crystals.

After, we immersed the mixture in an ice water bath for 5mins before we vacuum filtered to
collect the crystals as our end result. The result for acetanilide gave us 1.77g which we then
calculated to be 0.013 mole. We then calculated the percent yield to be 61.9% from the formula
% yield = a.y/t.y which we substituted actual yield to be 0.013 mole of acetanilide / 0.021 of
acetic anhydride.

Question:
a. Acetic acid is important because it acts as a catalyst and generates heat.
b. Water is important in this experiment to recrystallize the solvent.
c. Charcoal is important because it helps remove impurities since impurities attaches to the
activated carbon.