RECRYSTALLIZATION

Solo Experiment 1 – Individual Lab Report

(Save as pdf and submit by NOON, 1 week after your experiment)

Last Name: Malik

First Name: Hishmah

TA Name: Jane

Date Lab Performed: Monday, January 29, 2018

Date Lab Submitted: Sunday February 4, 2018

Group A or B or C: B

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(Please indicate if you performed the lab on a day other than your regularly scheduled day
and/or with a TA other than your regular TA).

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Chemistry 212 WINTER 2018

Solo Experiment 1: Recrystallization – Report Sheet

Data: (12 marks)

MP: 169 – 172 C

Reactants:
1.2 g
Amount p-aminophenol used: mass ________________ 0.0110 mol
mol ________________
1.2 g
Amount acetic anhydride used: mass ________________ 0.0118 mol
mol ________________
(Show Calculations)
n = mass/molarmass = 1.2/109.128 = 0.010996

1 mL = 1 g so 1.2 ml = 1.2 g

n = 1.2/102.089 = 0.01175

Product:
Theoretical Yield of Tylenol: 1.66 g
mass ________________ 0.0110 mol
mol ________________
(Show Calculations)
limiting reagant: p-aminophenol becuase it has fewer moles
1 mol p-aminophenol - 1 mol tylenol
109.128 g - 151.163 g
1.2 - x
x= 1.66 g (theoretical yield)
n = 1.66/151.163 = 0.01099 mol
Table 1. Recrystallization Data (6 marks)
Crude Tylenol Purified Tylenol

Yield (g) 1.14 1.08

Yield (%) (1.14/1.66)x100 = 68.7% (1.08/1.66)x100 = 65.1%

Appearance beige/offwhite solid white crystals

Melting Point 152 °C -163 °C 159 °C - 165 °C

Recovery (%) (1.08/1.14)x100 = 94.7 %

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Chemistry 212 WINTER 2018

Discussion Questions: (12 marks)

1. Given the following solubility test results, which would be the best recrystallization
solvent for Compound A? Why?
Ethanol: Cold – soluble; Hot – soluble
Water: Cold – insoluble; Hot – soluble
Benzene: Cold – insoluble; Hot - insoluble
The best recrystallization solvent for Compound A would be water, because it is soluble in hot water
but insoluble in cold water. This is necessary for recrystallization so that all of the impure compound
can dissolve in hot water but upon cooling crystals can form, leaving behind the soluble impurities. If
it were insoluble in both cold and hot conditions or soluble in both cold and hot conditions, it would
defeat the purpose of the recrystallization process which is entirely dependant on temperature and
differences in solubility.
2. How does recrystallization purify a solid?
In recrystallization, an impure compound is dissolved in a solvent and either the impurities
or the desired compound dissolves in the solvent. The other remaining substance stays in
solid form and can be removed from the solution. Temperature also plays an important role
in recrystallization procedures. Decreasing the temperature causes the solubility to
decrease. The impure substance will crystallize in a purer form and the impurities will be
left behind in the solution. After filtration the pure crystals can be dried and weighed.

3. Briefly explain the significance of your melting-point results (from table 1) in regards to
the purity of your crude and recrystallized product.
The melting point of a substance is the temperature range over which the first crystal starts to
melt until the last crystal completes its melting. A solid containing soluble impurities melts at a
lower temperature than the purified compound and a more pure compound also has a smaller
temperature range for the melting point. In this case, the melting point range of crude oil is
lower than the melting point range of the recrystallized the product because of the impurities
present in the crude product. Once the crude product is purified of these, the melting point
increases because pure compounds have a more ordered crystal lattice structure than impure
compounds. It is easier to melt substances with distorted lattices (due to different molecules),
explaining the lower melting point of the crude product (152-163°C)
4. Suggest one chemical reason (focus on chemical properties and reactivity), specific to
this experiment, why your percent recovery could be less than 100%.
In this experiment, the reaction between acetic anhydride and p-aminophenol is assumed to
completion but if some reactant was left unreacted, the amount of crude tylenol would not
be the same as expected. The sample size is also quite small which leaves more possibility
for indeterminate errors. Moreover, some impurities can be insoluble and therefore increase
the mass of the “purified” tylenol, thereby affecting the recovery volume. Another source of
error that could affect the the recovery is the loss of residue during the process of
transferring/weighing the solid.

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