Aspirin

level 4
GULSHAD AHMAD

Aims
In level 4, you'll find out about synthesising aspirin using different reagents. You will use thin layer chromatography
(TLC) to identify which reactants produce aspirin and decide the best reaction to produce aspirin on an industrial scale.

In each activity you'll be able to collect points. At the end of the level you can restart to improve your skills.

Video 100 Points

Comprehension 70 Points 4 Attempts

Ethanoic anhydride is the electrophilic reagent in aspirin synthesis.

Ethanoic anhydride can be replaced with a different reagent when making aspirin.

When an alternative electrophilic reagent is used to make aspirin the leaving group changes.

When ethanoic anhydride is replaced with a more reactive reagent it reduces the reaction time.

To make industrial production as environmentally friendly as possible energy use should be minimised.

Reactants 50 Points 5 Attempts

Ethanoic anhydride and ethanoyl chloride can both be used to make aspirin because they both have good enough
leaving groups to undergo esterification. The formation of aspirin can be seen by TLC (A: 2-Hydroxybenzoic acid, B:
Aspirin).

Leaving groups 50 Points 5 Attempts

For ethanoic anhydride the leaving group is an ethanoate ion and for ethanoyl chloride the leaving group is a chloride
ion. Good leaving groups have electronegative atoms and must form stable anions.
Reagents 50 Points 5 Attempts

Ethanoic anhydride is chosen over ethanoyl chloride for industrial production of aspirin because:

ethanoic anhydride is less hazardous than ethanoyl chloride

ethanoic anhydride is cheaper.

Review
Things I did well on:

Things I could improve on:

You have identified ethanoic anhydride as the best reagent for the industrial scale synthesis of aspirin. Can you
remember why?