WM What's in a Medicine?

WM1 Synopsis

A study of aspirin, its chemistry and synthesis, illustrating some of the features of the history of pharmaceuticals and the pharmaceutical industry. Main topics:

• medicines based on natural products;

• identification of the active principle of aspirin by spectroscopic methods;

• chemical aspects of aspirin;

• synthesis of salicylic acid and aspirin;

• formulation and delivery of medicines;

• development and testing of medicines.

 

WM2 Learning outcomes

Candidates should be able to:

(a)

recognise members of the following homologous series: phenols, acyl chlorides, esters;

(b)

use systematic nomenclature to name carboxylic acids and esters;

(c)

describe and explain the acidic nature of carboxylic acids;

 

(d)

describe and explain the reaction of alcohols with carboxylic acids to form esters;

(e)

 

describe and explain the following properties of phenols :

 

 

(I)

(ii)

(iii)

acidic nature,

test with iron (III) chloride solution

reaction of phenols with acyl chlorides to form esters

(f)

 

account for the increasing relative strengths as acids of alcohols, phenols and carboxylic acids.

(g)

recall the technique of heating under reflux for reactions involving volatile liquids;

(h)

recall the technique of thin layer chromatography (t.l.c.) and interpret results;

(i)

describe how the following forms of spectroscopy can be used for the elucidation of

 

molecular structure:

 

 

(a)            mass spectrometry (m.s.),

(ii)                 infrared spectroscopy (i.r)

 

(j)

interpret mass spectra (molecular ion and significance of the fragmentation pattern)

 

for salicylic acid and simple compounds containing a limited range of functional

 

Groups (hydroxyl, carbonyl, carboxylic acid and ester groups) given relevant information;

 

 

(k)

interpret infrared spectra for salicylic acid and simple compounds containing a limited 

 

Range of functional groups (hydroxyl, carbonyl, carboxylic acid and ester groups) given relevant information.

 

(l)

show awareness that more effective medicines can be obtained by modifying the structure of existing medicines.

(m)

 

show awareness of the procedures used in developing and establishing the safety of a medicine.