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Acid Base
Acid Base
NAME:
DATE:
MARK:
E-mail:
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:
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.