Purification of Acetanilide via

Recrystallization

CHEM 200 (ORGANIC CHEMISTRY LAB)

A.Y. 2016-2017
RECRYSTALLIZATION
One of the most common purification technique of organic
compounds
Separation works on the basis of the difference in solubility
The process involves dissolution of the solid in an
appropriate solvent at an elevated temperature and the
subsequent reformation of the crystals upon cooling.
This technique is also called solution recrystallization.
Recrystallizing solvent act as an intermediate that
separates the pure compound from the impure component of
the mixture.
 Key Recrystallizing Concepts
Choosing Recrystallization solvent - A good solvent for recrystallization is one that
your compound not very soluble in at low temperatures, but very soluble in at higher
temperatures.
Like dissolves like Polar compounds to polar solvents and non polar compounds to
non polar solvents.
Crystal size and cooling speed. The speed at which you allow a saturated solution to
cool affects the size of the crystals that form! If you take a hot solution and slam it into
an ice bath, youll get smaller crystals. If you allow a hot solution to cool without any
added heat for 10-20 minutes, and then place it in an ice bath, youll get larger crystals.
The cool incubation set up of gravimetric filtration while doing the recrystallization
process acts as heat stabilizer to prevent bumping of the excess heat generated during
the separation and also to avoid sudden pressure build up while changing incubation
state from warm to cool set up.
The last filtration method uses fluted filter paper to enhance the generation of fine and
pure crystals for further analysis
Steps in Solution Recrystallization
1. Selection of an appropriate solvent
2. Dissolution of the solid to be purified in the
solvent near or at its boiling point
3. Decoloration with an activated carbon if the
solution is colored to remove impurities
4. Formation of crystalline solid from the
solution as it cools.
5. Isolation of the purified solid by filtration

6. Drying the crystals.

Synthesis of Acetanilide from Aniline and Acetic Anhydride

In the reaction above:

Limiting reactant: Aniline
A substance that stoichiometrically limits the amount of
product that can be formed in a reaction.
 Calculating Theoretical Yield and Percentage Yield
Theoretical yield = the maximum amount of a specified
product that could be obtained from specified amounts of
reactants, assuming complete consumption of the limiting
reactant according to only one reaction and complete recovery
of the product.
Actual yield = the amount of a specified pure product actually
obtained from a given reaction.
Percentage yield = 100% times actual yield divided by
theoretical yield.
 SAMPLE CALCULATIONS
Problem: A 15.6 g sample of C6H6 is mixed with excess HNO3. We isolate 18.0 g
of C6H5NO2. What is the percent yield of C6H5NO2 in this reaction?
Given: 15.6 g of C6H6 (MW: 78.10 g/mole)
18.0 g of C6H5NO2 (MW: 123.10 g/mole)
Plan: First, calculate the theoretical yield of the reaction.

___g of C6H5NO2 = 15.6 g X 1 mole C6H6 X 1 mole C6H5NO2 X 123.1 g C6H5NO2

78.1 g C6H6 1 mole C6H5NO2 1 mole C6H5NO2
= 24.6 g C6H5NO2 theoretical yield
 SAMPLE CALCULATIONS
Problem: A 15.6 g sample of C6H6 is mixed with excess HNO3. We isolate 18.0 g
of C6H5NO2. What is the percent yield of C6H5NO2 in this reaction?
Given: 15.6 g of C6H6 (MW: 78.10 g/mole)
18.0 g of C6H5NO2 (MW: 123.10 g/mole)
Plan: First, calculate the theoretical yield of the reaction.

___g of C6H5NO2 = 15.6 g X 1 mole C6H6 X 1 mole C6H5NO2 X 123.1 g C6H5NO2

78.1 g C6H6 1 mole C6H5NO2 1 mole C6H5NO2
= 24.6 g C6H5NO2 theoretical yield

% Yield = Actual yield X 100% = 18.0 g C6H5NO2 X 100% = 73.2 %

Theoretical yield 24.6 g C6H5NO2
 SAMPLE CALCULATIONS
Problem: The percent yield for the reaction PCl3 + Cl2 = PCl5 is 86.5%. What mass of
PCl5 is obtained from the reaction of 96.7 g of PCl3 with excess chlorine?
Given: % yield of the reaction = 86.5 % (In grams: 86.5 g)
96.7 g of PCl3 (MW: 137.5 g/mole)
Plan: The unknown here is the actual yield. We need to calculate first the theoretical
yield of the reaction based on the reaction equation and given problem.
___g of PCl5 = 96.7 g X 1 mole PCl3 X 1 mole PCl5 X 208.5 g PCl5
137.5 g PCl3 1 mole PCl3 1 mole PCl5
= 146.6 g PCl5 theoretical yield
Then finally, we can now compute for the actual yield using the calculated
theoretical yield:
X g Actual yield = Theoretical yield X %yield/100% (0.865)
X g Actual yield = 146.6 g PCl5 X 0.865 = 126.8 or 127 g actual yield.
END of DISCUSSION