Aim: To purify crude benzoic and impure acetanilide through recrystallization in order to determine

the melting point for both substances as well as to determine the percent recovery.
Experimental:
Chemicals: Equipment:
Name Structure Physical
Acetanilide Solid,
M.P = Procedure:
114° A literature procedure was followed with the
Reagents: following modifications
NaCl (Salt), Sand, M.W =
135 a. a mixture that contains sand, salt and
Water acetanilide
g/mol Capillaries was used instead of activated
Benzoic Solid, charcoal.
acid M.P = b. a Hirsch funnel was used for the
Mel-Temp vacuum
Apparatus
122° filtration instead of a short-stem glass funnel
M.W =
122
Setup:
g/mol
Chemical Reaction/Mechanism:

5 6 5 6
4 7 4 7

3 8 3 8

2 9 2 9
1 11 1 10

Vacuum filtration,
Erlenmeyer flask,
Ice Bath,
Clamp and Stand
Hot Plate
Data:
After 1st filtration
Weighing Paper Only (g) 0.2377
Weighing Paper with Acetanilide (g) 1.2530
Acetanilide Only (g) 1.0153

After 2nd filtration

Weighing Paper Only (g) 0.2410
Weighing Paper with Acetanilide (g) 0.2422
Acetanilide Only (g) 0.0012

Melting Point Melting Point Range

Benzoic (pure) 120 119-121
Acetanilide (impure) 101 98-104

Results:
Acetanilide (impure)
Percent Recovery 0.12%
Moles of product 8.87 · 10-6 mol

Percent Recovery:
0.0012
∗100=0.11819 % ≈ 0.12%
1.0153

Moles of Product:
0.0012 g
=0.00000887=8.87 · 10-6 mol
135.17 g
Discussion:
Reference:

Organic Laboratory Manual, Shanbhag & Veliz, pg. 15-23, Nova Southeastern University, 2012.

Question:
1. What happens to the impurities in a recrystallization? In other words, how are soluble
impurities removed during a recrystallization?
During recrystallization, the impurities are being removed and the soluble impurities are
removed by when the mixture is dissolved in the solvent during heating the mixture, the
solubility of the compound would decrease which leaves the purity of the product by itself.
2. Why is water a good solvent for the recrystallization of acetanilide?
Water is a good solvent for the recrystallization because acetanilide dissolve very easily when
the water is hot. However, if the water is cold, the product would be insoluble.

3. How did the melting point of your acetanilide change after

recrystallization?
The melting point of the acetanilide change after recrystallization by the temperature
decreasing which means that the product is still impure (higher temperature indicates purity of
the product).
4. Why could you test the purity of your acetanilide by mixing it with
a known, pure sample of acetanilide and rechecking the m. p.?
I could test the purity of acetanilide by mixing it with a known, pure sample of acetanilide
because I can compare the values of the melting points to see if the melting point of impure
acetanilide is close to the expected range of the pure substance.

5. Why must the funnel be heated before the hot acetanilide solution
is filtered?
The funnel must be heated before the hot acetanilide solution is filtered because it won’t clog
the funnel. In other words, if the funnel wasn’t heated, then crystallization would occur before
it supposed to which would affect the crystals (in order to find the percent recovery).

6. What purpose does adding activated charcoal during

recrystallization serve?
The purpose of adding activated charcoal during recrystallization to remove the impurities in
the solution because the activated charcoal as a reagent.

7. What is the difference between percent recovery and percent yield?

The percent recovery is to measure the data from recrystallization while percent yield is to
measure the data from chemical reactions.

8. Melting “point” is a misleading term. Why?

Melting “point” is a misleading term because the melting point isn’t consistent once the solid
turns to liquid. For instance, the substance can start to sweat at 100° then it would turn to liquid
in 101° and then the temperature would continue to rise because of pressure changes.