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Carboxylic Acid
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Functional Group:
Carboxyl
First 3 Members:
1. Carboxylic Acids are weak acid.
2. The functional group of carboxylic acids is carboxyl group.
3. When dissolve in water, the carboxyl group will ionise to produce a hydrogen ion.
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1. The greater the number of carbons in the molecule, the higher the boiling point of a carboxylic
acid.
2. The boiling points of carboxylic acids are higher than the alcohols of same number of carbons.
Solubility in water
1. The small molecule carboxylic acid such as methanoic acid and ethanoic acid are soluble in
water.
2. The solubility of the bigger acids decreases as the size of the molecule increases. This is because
the longer hydrocarbon “tails” of the molecules get between water molecules and break
hydrogen bonds.
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1. Alcohols can be oxidised to carboxylic acids using potassium dichromate(VI) solution in the
presence of dilute sulphuric acid.
2. Chemical Equation below represents the reaction.
→
C2H5OH+2[O] CH3COOH + H2O
3. The figure below shows the apparatus set up to prepare ethanoic acid.
4. The mixture is heated under reflux to prevent the ethanol to evaporate and escape to the
surrounding before it has time to be oxidised to the carboxylic acid.
5. Ethanol vapour will condense into liquid in the Liebig condenser and flow back into the flask to
complete the reaction.
6. The mixture is heated by using a water bath:
a. to keep the temperature constant
b. to ensure a uniform heating (heat is evenly supplied)
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Carboxylic acids react with the more reactive metals to produce a salt and hydrogen.
HCOOH + Mg → Mg(HCOO) + H 2 2
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As other acids, carboxylic acids react with carbonate metal to produce a salt, water and carbon
dioxide.
Neutralisation
As other acids, carboxylic acids react with base oxide or alkali to produce salt and water.
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Esterification
Carboxylic acid reacts with alcohol with the presence of .concentrated sulphuric acid as catalyst to
produce ester and water.
Carboxylic Acids + Alcohol → Ester + Water
Example:
CH3COOH + C2H5OH→ CH COOC H + H O
3 2 5 2
CH COOH + CH OH → CH COOCH + H O
3 3 3 3 2
CmH2m + 1COOCnH2n + 1
where
m = 0, 1, 2, 3
n = 1, 2, 3
Example
Ester Formula
Methyl methanoate
HCOOCH3
(m=0, n=1)
Ethyl methanoate
CH3COOCH3
(m=1, n=1)
Ethyl ethanoate
CH3COOC2H5
(m=1, n=2)
Propylethanoate
C2H5COO C2H5
(m=2, n=2)
Functional group:
Formation:
1. Esters are produced when carboxylic acid reacts with alcohol in the presence of concentrated
sulphuric acid as a catalyst.
2. This reaction is called the esterification reaction.
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Chapter 1