Carboxylic Acids - OCR

Revision notes on carboxylic acids (Chains, Ring and Spec) for A2 Chemistry.

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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 + Water
E.g.2.
Ethanoic acid + Calcium Hydroxide Calcium Ethanoate + H2O
2CH3COOH + Ca(OH)2 + 2H2O
b) Acid + Carbonate Salt + CO2 + H2O
2CH3COOH + Na2CO3 2CH3COO­Na+ + CO2(g) + H2O
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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. Ethanoic Acid + PCl5 + HCl + POCl3
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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 + [4] CH3CH2OH + H2O
Esters
Hydrolysis of an Ester
Ester + H2O Alcohol + Carboxylic Acid
a) Acid catalysed hydrolysis of an ester
Propyl ethanoate + H2O
Propene + Ethanoic Acid
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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 reactions are very violent and spit
HCl is given off and as observation seen as `Misty white Fumes'
Acyl­Chlorides react with anything that has a H in its functional group
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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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