07cowanl
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The different aspects of aspirin

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07cowanl
Created by 07cowanl over 6 years ago
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Aspirin
1 How its made
1.1 Salicylic acid + ethanoic anhydride --> Aspirin + Ethanoic acid
1.1.1 Heat under reflux
1.2 Salicylic acid + Ethanoyl Chloride --> Aspirin + Hydrogen Chloride
1.2.1 Catalyst of Conc. Sulphuric Acid and heat under reflux
1.2.2 Not a common reaction as Acyl Chlorides are nasty chemicals to work with.
1.3 Both reactions must take place in a fume cupboard
1.4 Salicylic acid is found in willow bark
2 Structure
2.1 Benzene ring with functional groups on position 1 and 2.
2.2 The angle around the O-C=OCH3 is 120, as there are 3 groups of electrons around the central carbon.
2.3 2-ethanoylhydroxylbenzoic acid
3 Formula
3.1 Contains a benzene ring.
3.2 Benzene with a COOH group on position 1, and a OC=OCH3
3.3 C9H8O4
3.4 Systematic nomenclature- 2-ethanoylhydroxylbenzoic acid
4 Associated Chemicals
4.1 Salicylic Acid
4.1.1 Found in willow bark
4.1.2 Consists of a benzene ring with a carboxylic acid functional group on position 1, and an alcohol functional group on position 2
4.1.3 2-hydroxybenzoic acid
4.1.4 Salicylic acid contains a phenol group, so will not react with Carboxylic acids to make esters, hence why we use ethanoic anhydride orethanoyl chloride to make Aspirin.
4.1.4.1 Phenol groups can be detected by using Iron (III) Chloride. If it goes dark purple then there is a phenol group present. If it stays orange then there is no phenol group.
4.2 Oil of Wintergreen
4.2.1 If Salicylic acid is reacted with Methanol instead of an ethanoic anhydride or ethanoyl chloride then it forms oil of wintergreen, which also has painkilling qualities.
4.2.1.1 Oil of Wintergreen is also an ester, like Aspirin, however the carboxylic acid functional group has reacted this time, instead of the alcohol group, so a different ester is formed.
4.3 Ethanoic Anhydride
4.3.1 This is the most used chemical to react with salicylic acid to make Aspirin.
4.3.2 Formed when 2 ethanoic acid molecules react to form ethanoic anhydride and water.
4.3.2.1 Condensation reaction
4.4 Ethanoyl Chloride
4.4.1 Formed when ethanoic acid and hydrogen chloride react to form ethanoyl chloride and water.
4.4.1.1 Substitution reaction
4.4.2 Not commonly used to react with salicylic acid to make Aspirin as it is a nasty chemical to handle.

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