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PHARMACEUTICAL CHEMISTRY EXPERIMENT 4: ACID-BASE

REPORT TO BE SUBMITTED THROUGH BLACKBOARD WITHIN 1 WEEK
OF PERFORMING THE PRACTICAL
This data sheet must be handed in to a demonstrator at the end of the practical.
At the end of the experiment, clean up your bench and get the demonstrator to
sign your script.
Up to 2 marks may be deducted from the total mark as a penalty for an unclean
bench.
COSHH & SAFETY (must be completed BEFORE you enter the lab; 1 mark).

Irritants:
2M HCl, 2M NaOH & citric acid are very harmful to eyes and skin. Also
penicillin G and aspirin are mild irritants.
Barbitone and aspirin are harmful if ingested.
Precautions:
Wear safety goggles and gloves at all times. Do not touch mouth or eat, in
order to avoid swallowing chemicals. Clean spillages immediately.
Disposal:
Citric acid, penicillin, aspirin, barbitone- specially designated waste bottles.
HCl & NaOH- sink, excess water.
Other points:
Using glassware- handle carefully to avoid serious potential injury.

EXPERIMENTAL RESULTS
(To be completed and assessed during the practical)
1. Enter the results on solubility of the studied medicines or natural products (i.e.
Penicillin G, Citric Acid, Sulphanilamide, Ascorbic Acid, Aspirin, Tryptamine,
Barbitone and L-Phenylalanine) in 2M NaOH, water and 2 M HCl into Table III.
(3 marks)

2. Enter the measured pH values of the media for each condition (i.e. after the
addition of 2M NaOH, water or 2M HCl to each drug) into Table III.
(1 mark)
This data sheet must be handed in to a demonstrator at the end of practical for
assessment.

Table III. The effect of acids and bases on the solubility of medicinerelated substances.
2M NaOH

Water

2M HCl

Natural Product
or Medicine
Solubility

Media
pH

Penicillin G

Citric Acid

Sulphanilamide

Ascorbic Acid

Aspirin

Tryptamine

Barbitone

L-Phenylalanine

Solubility

Media
pH

Solubility

Media
pH

DATA ANALYSIS
(To be completed within 1 week of performing practical)
2.

Using the chemistry drawing package ChemDraw Ultra draw the chemical
structures of the studied medicines or natural products (i.e. Penicillin G, Citric
Acid, Sulphanilamide, Ascorbic Acid, Aspirin, Tryptamine, Barbitone and
Phenylalanine) and paste the structures below:
(4 marks)

COOHgroupsionised
inwater&NaOH

NH2groups
protonatedin
water&HCl

COOHgroups
ionisedinwater&
NaOH

COOHgroups
ionisedinwater&
NaOH

NH2
groups
protona
tedin
water
&HCl

NHgroupprotonatedin
water&HCl

COOHgroup
ionisedinwater&
NaOH

PenicillinG

COOHgroupionised
inwater&NaOH

NH2group
protonatedin
water&HCl

Barbitone

3.

Identify any acidic and/or basic functional groups in the structure of each
studied drug that can potentially be ionised or protonated in (i) neutral
conditions (WATER), (ii) in the presence of strong base (2M NaOH) and/or (iii)
in the presence of strong acid (2M HCl). Indicate these functional groups and
corresponding pKa values (where appropriate) by using suitable annotations
next to the structures of the studied compounds.
(2 marks)

4.

Using the chemistry drawing package ChemDraw Ultra draw, paste below the
predicted PREDOMINANT ionisation states of each drug in (i) neutral conditions
(WATER), (ii) in the presence of strong base (2M NaOH) and (iii) in the
presence of strong acid (2M HCl).
(4 marks)

Neutral conditions:

Acidic conditions:

Alkaline conditions:

5. Based on the predicted PREDOMINANT ionisation state of each dug indicate

whether you expect this substance to be soluble in acid, base or water. Compare
your predictions with the experimental observations obtained in PCE 4
experiment and discuss any discrepancies. (Hint: you may wish to consider the
media pH values measured in each experiment; see Table III).
(4 marks)
Citric acid:
In water, it ionises and should therefore dissolve in the polar solvent.
In NaOH, it again ionises and should dissolve.
In HCl, the COOH group does not ionise, so the solubility is determined by the the
polar and non-polar components. As it contains 3 COOH groups and a relatively
short non-polar chain, it should be able to form hydrogen bonds with water
molecules and therefore dissolve.
Sulphanilamide:
In water, it is protonated and should therefore dissolve in the polar solvent.
It does not ionise in NaOH and should not be soluble.
It is protonated in HCl and should therefore be soluble.
However it was insoluble in all the solvents. This may be due to the non-polar
benzene ring, which breaks hydrogen bonds in water at the same time that the
NH2 groups form them.
Penicillin G:
In water, the COOH group and amine group ionise, so it should be soluble.
In NaOH, the COOH group ionises, so it should be soluble.
In HCl, it does not ionise so it should be insoluble.
Aspirin:
In water, the COOH group ionises so it should be soluble. However, it was proved
to be insoluble in the experiment; this may be due to the non-polar benzene ring.
In NaOH, it is ionised so should be soluble.
In HCl it does not ionise, so will be insoluble.
Ascorbic acid:
It ionises in water and should therefore be soluble.
It ionises in NaOH and should therefore be soluble.
It does not ionise in HCl so should be insoluble. However it was soluble, which may
be due to the many hydrophilic functional groups, i.e. OH
Tryptamine:

It is protonated in water, so should be soluble.

It does not ionise in NaOH, so should not be soluble.
It is protonated in HCl, so should be soluble.
However it was insoluble in all the solvents, which may be due to the presence of
large non-polar groups such as the benzene ring.
Barbitone:
It is not protonated in water, so should not be soluble.
It is ionised in NaOH, so should be soluble.
It does not ionise in HCl, so should not be soluble.
L-Phenylalanine:
It is ionised in water, but has no overall charge so should not be soluble.
It is ionised in NaOH so should be soluble.
It is protonated in HCl so should be soluble.

6.

CPD: Briefly discuss the significance of the experiments you carried out during
this practical session. How useful could this knowledge be for your future role
as a Pharmacist?
(1 mark)

The experiment helped to demonstrate the effect of pH and ionisation on the solubility of
a drug, and how particular functional groups may contribute to the solubility or insolubility
in various solvents. This could be useful in future, particularly if working as an industrial
pharmacist where buffers and functional groups need to be considered to maximise the
efficacy of the drug.