Student worksheet

Activity 5: The synthesis of antifebrin

Objective
Be able to manipulate materials and equipment with
care and precision.
Be able to follow instructions and produce a good yield
of pure antifebrin.

Safety

Perform the experiment in a

well-ventilated room

Wear a lab coat and nitrile

disposable gloves and tie
long hair back.

Wear goggles while mixing

solutions.

Antifebrin is harmful if
swallowed.

Toxic

Flammable

Corrosive Harmful

Procedure
1. Dissolve 1.5g of phenylammonium chloride in 25cm3
of water in a 100cm3 beaker.
2. Prepare a solution of sodium ethanoate in another 100
cm3 beaker by dissolving 5g of sodium ethanoate in 25
cm3 of water.
3. Carefully add 3.0cm3 of ethanoic anhydride to the
solution of phenylammonium chloride while stirring.
4. Add the sodium ethanoate solution and continue to stir
for five minutes.
5. Filter the crude product from the mixture under reduced
pressure and wash with a minimum volume of iced
water.
6. Recrystallise the antifebrin using hot water as your
solvent. Take care to use the minimum volume
necessary. Filter the pure crystals under reduced
pressure and dry the crystals at room temperature.
7. Find the mass of your product.
8. Use a small sample of your product to determine its
melting point.
9. Record your data in a suitable format.

Equipment/materials
1.5g phenylammonium chloride (toxic, prolonged
exposure should be avoided)
5g sodium ethanoate (low hazard)
3cm3 ethanoic anhydride (corrosive, flammable and
harmful by inhalation)
Three 100cm3 beakers
10cm3 measuring cylinder

25cm3 measuring cylinder

Spatulas

Two stirring rods

Distilled/deionised water

Ice
Access to vacuum filtration, a balance, melting point
apparatus and boiling water

Data/diagram
H = 1.0, C = 12.0, N = 14.0, Cl = 35.5 and O = 16.0

The density of ethanoic anhydride is 1.08gcm3.

Analysis of results
C6H5NH3+Cl + (CH3CO)2O CH3CONHC6H5 +
CH3COOH + HCl
Calculate the mass of the ethanoic anhydride used
and show by calculation that the ethanoic anhydride
is in excess.
Using the above equation and data, and the mass of
phenylammonium chloride, calculate the percentage
yield of the antifebrin.
From the examiner
Demonstrate skilful and safe practical techniques.

Record measurements to an appropriate precision.

Consider the accuracy of your data before deciding
on the number of significant figures for the answer.

Questions
1. Other than the benzene ring, what is the functional group present in antifebrin?
2. Name two other series of compounds that contain this functional group.
3. An infrared spectrum of antifebrin (produced by this method) had a broad absorption between 25003300 cm1. What
do you think was the main impurity present in the antifebrin? Give your reason.
4. Find the melting point of pure antifebrin (ask your teacher for this data if you cannot find it). Comment on the purity of
your sample by comparing your melting point with the actual value and explain any differences.
5. Compounds such as antifebrin have unusually high melting points. Discuss the type of bonding between the molecules
that might give rise to this phenomenon.
Practical activities have been checked for health and safety advice by CLEAPSS. All users will need to review the risk
assessment information and may need to adapt it to local circumstances.

Pearson Education Ltd 2009

This document may have been altered from the original

5/29

Teacher worksheet

Activity 5: The synthesis of antifebrin

Objective
Be able to manipulate materials and equipment with
care and precision.
Be able to follow instructions and produce a good yield
of pure antifebrin.
Safety
Perform the experiment in a wellventilated room
Wear a lab coat and nitrile
disposable gloves and tie long hair
back.
Wear goggles while mixing
solutions.
Antifebrin is harmful if swallowed.
Phenylammonium chloride is toxic
and prolonged exposure should be
avoided.
Ethanoic anhydride is corrosive,
flammable and harmful by
inhalation.

Toxic

From the examiner

Demonstrate skilful and safe practical techniques.

Record measurements to an appropriate precision.

Consider the accuracy of your data before deciding
on the number of significant figures for the answer.

Analysis of results and answers

Mass of ethanoic anhydride = 3.24g
Mr C6H5NH3+Cl = 129.5
Mr (CH3CO)2O = 102
Moles C6H5NH3+Cl = 1.5/129.5 = 0.012 moles

Flammable

Moles (CH3CO)2O = 3.24/102 = 0.032 moles

Corrosive

Harmful

Notes on procedure
1. Dissolve 1.5g of phenylammonium chloride in 25cm3
of water in a 100cm3 beaker.
2. Prepare a solution of sodium ethanoate in another 100
cm3 beaker by dissolving 5g of sodium ethanoate in 25
cm3 of water.
3. Carefully add 3.0cm3 of ethanoic anhydride to the
solution of phenylammonium chloride while stirring.
4. Add the sodium ethanoate solution and continue to stir
for five minutes.
5. Filter the crude product from the mixture under reduced
pressure (if your school does not have the required
water pressure use a hand pump) and wash with a
minimum volume of iced water.
6. Recrystallise the antifebrin using hot water as your
solvent. Take care to use the minimum volume
necessary. Filter the pure crystals under reduced
pressure and dry the crystals at room temperature.
7. Find the mass of your product.
8. Use a small sample of your product to determine its
melting point.
9. Record your data in a suitable format.

Ratio C6H5NH3+Cl : (CH3CO)2O

1
:
1
(CH3CO)2O is in excess.

1 mole C6H5NH3+Cl gives:

1 mole CH3CONHC6H5
Mr C6H5NH3+Cl = 129.5

Mr CH3CONHC6H5 = 135
No of moles of C6H5NH3+Cl = 1.5 129.5

Expected yield of CH3CONHC6H5 = 1.5 129.5

moles
Actual yield = students mass 135 moles

% yield = (actual yield expected yield) 100

Melting point of antifebrin is 115C.

1. The amide group
2. Proteins/polypeptides and polyamides
3. Ethanoic acid. The absorption is due to the OH bond
(hydrogen bonded in carboxylic acids).
4. If the students sample has an m.pt. that is within 12
C of the actual m.pt., this implies that the sample is
pure. The lower the m.pt. (as compared with the pure
antifebrin), the lower the purity.
5. The amide group has two polar bonds: the C=O; and
the NH bonds. This means that the hydrogen in the
NH bond in one molecule can form a hydrogen
bond with the O in a C=O bond in an adjacent
molecule. This type of intermolecular bonding will
require additional energy to break these bonds,
resulting in an increased melting point.

Practical activities have been checked for health and safety advice by CLEAPSS. All users will need to review the risk
assessment information and may need to adapt it to local circumstances.

Pearson Education Ltd 2009

This document may have been altered from the original

5/29

Technician worksheet

Activity 5: The synthesis of antifebrin

Objective
Be able to manipulate materials and equipment with
care and precision.
Be able to follow instructions and produce a good
yield of pure antifebrin.

Safety

Perform the experiment in a well-ventilated room

Wear a lab coat and nitrile disposable gloves and tie

long hair back.

Wear goggles while mixing solutions.

Antifebrin is harmful if swallowed.

Requirements per student*/group of students

Notes

1.5g phenylammonium chloride

Toxic, prolonged exposure should be avoided

Should be placed in a fume cupboard and gloves w

handling
5g sodium ethanoate

Low hazard

3cm3 ethanoic anhydride

Corrosive, flammable and harmful by inhalation

Should be placed in a fume cupboard and gloves w

handling
150cm3 distilled/deionised water
Ice
Three 100cm3 beakers

Two for preparing the solutions and one for recrysta

10cm3 measuring cylinder

25cm3 measuring cylinder
Spatulas
Stirring rods
Mass balance accurate to 0.01g and weighing boats
Buchner funnel, Buchner flask with water (suction) pump
and filter paper to fit funnel
Melting point apparatus and melting point tubes
Kettles for hot water

Notes
Students should have access to a kettle to provide them with boiling water for step 6.
CLEAPSS Hazcards (4A and 39) should be consulted and a risk assessment carried out using up-to-date information
before this practical is carried out.

Practical activities have been checked for health and safety advice by CLEAPSS. All users will need to review the risk
assessment information and may need to adapt it to local circumstances.

Pearson Education Ltd 2009

This document may have been altered from the original

5/29