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01/10/07

Carboxylic Acids and their Derivatives




Carboxylic Acids

Chemical Properties of Carboxylic Acids

They Behave as Acids
Acid ­ `Proton (H+) Donor'

a) Acid + Base Salt + water

Ethanoic acid + NaOH Sodium Ethanoate + Water
CH3CH2OH + NaOH CH3COO­Na+ + H2O




E.g.1.
Benzoic acid + KOH Potassium Benzoate…

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c) Acid + Reactive metal Salt + H2(g)
CH3COOH + Na CH3COO­Na+ + H2(g)

­ Ethanol + Na Sodium ethoxide + ½H2(g)
CH3CH2OH + Na CH3CH2ONa + ½H2

d) Alcohols + Carboxylic Acids Ester + H2O




2Ethanol + Benzene-1,4-dioic Acid Diethyl
Benzene-1,4-dioate




e) Carboxylic Aid + Chlorinating Agent Acyl(Acid)chlorides

i.…

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ii. Ethanoic Acid + SOCL2 + HCl + SO2




Very reactive and used to make other chemicals
o `good synthetic chemical'
o `Lachromatory' ­ Makes you cry

f) Carboxylic Acids can be reduced


Carboxylic Acids are difficult to reduce
o need a powerful reducing agent, LiAlH4 (non aq)




CH3COOH +…

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b) Base catalysed hydrolysis of an ester
Propyl ethanoate + H2O
Propene + Ethanoic Acid




The carboxylic acid will react with the base to form a salt once the hydrolysis reaction is done

Acid + Base + Alcohol Salt + Alcohol




Acyl­Chlorides (Acid ­ Chlorides)

Chemical properties of Acyl­Chlorides


All…

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3. Making an Ester

Methyl Propanoyl Chloride + TriChloroPhenol TriChlorophenyl MethylPropanoate




­ This is 100% conversion, there is no equilibrium state

4. Manking a Peptide

Ethanoyl Chloride + Ethylamine EthylEthanamide




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