Experiment No.

3
SYNTHESIS OF ACETANILIDE

I. Materials and equipment

Equipment/Apparatus

Pipette
Graduated cylinder Mettler balance
Beaker Casserole
Erlenmeyer flask Aspirator
Melting point apparatus Capillary tubes
Hot plate Buchner funnel
Ice bath Watch glass
Suction pump

Chemicals

Aniline
Hydrochloric acid
Charcoal
Sodium acetate trihydrate
Acetic anhydride

III. Special instructions

1. Read on the physical properties of the intermediates and the product.

COMPOUND CHARACTERISTICS
Conc. HCl Irritant, corrosive
Aniline Irritant to the eyes and skin, harmful if ingested and
inhaled and a possible carcinogen
Sodium acetate Irritant to the eyes and skin
Sodium bicarbonate Irritant especially to respiratory system

2. Compute for the amounts (in grams or milliliters) of other reactants and reagents based
on the amount of starting material that is assigned.

IV. Procedure
A. Synthesis
1. Place 2 ml of acetyl chloride in a flask
2. Add carefully 1 ml of aniline.
3. Heat the flask gently for about 2 minutes.
 4. Pour the product into 10 ml of water.
5. Filter off the crystals.
6. Wash once with 3 ml of 3N hydrochloric acid and twice with water.
7. Dry the crystals and weigh.
8. Calculate the % yield of the product.

B. Chemical Tests
a. Hydrolysis of acetanilide. Place 1 g of the acetanilide in a test tube and add 3 ml of
concentrated hydrochloric acid. Boil the solution carefully for 1 minute. Cool, dilute with
water, and note the appearance of crystals.
b. Bromination. Place 1 g of acetanilide in a test tube and add 5 ml of water and 0.1 ml of
concentrated HCl. Add bromine water until solution assumes a distinctly yellow color.
Repeat the procedure using aniline as the sample. Compare the volume of bromine water
necessary to produce a yellow colored solution.

VI. Data and results

Balanced reaction:

Experimental data

Reactants Molecular weight Density Amount used

Products Molecular weight Amount produced

Calculations:

Actual Yield ___________________

Theoretical Yield ___________________
Percentage Yield ___________________
 Solution:

Results

Identification Tests:
A Physical Tests
1. Appearance ________________________
2. Odor ________________________

B. Chemical Test Result Photo

VII. Answer to questions

1. What is the chemical name of acetanilide? Give its reaction to litmus?

2. How does the structure of amine differ from that of amide?
3. Name the structure or functional group commonly present in the following drugs (draw the
structure and identify by encircling):
a. aspirin
b. acetaminophen
c. ibuprofen
d. naproxen
e. ketoprofen
4. What are the undesirable effects of acetanilide that make it toxic? Explain the
biotransformation of acetanilide.