3.3.9: Carboxylic acids
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cWhat is the functional group of carboxylic acids? (1)
The functional group of carboxylic acids is -COOH
How are carboxylic acids made? (2)
• Carboxylic acids are made by oxidising a primary alcohol to an aldehyde. • It is then further oxidised to form the carboxylic acid
Write the general reaction for the oxidation of a primary alcohol to an aldehyde. (1)
RCH2OH + [O] → RCHO + H2O
Provide an example of a primary alcohol being oxidized to an aldehyde. (1)
CH3CH2OH + [O] → CH3CHO + H2O
Write the general reaction for the oxidation of an aldehyde to a carboxylic acid. (1)
RCHO + [O] → RCOOH
Provide an example of an aldehyde being oxidised to a carboxylic acid. (1)
CH3CHO + [O] → CH3COOH
Write the overall reaction for the formation of a carboxylic acid from a primary alcohol. (1)
CH3CH2OH + 2[O] → CH3COOH + H2O
Draw the structure of 3-aminopropanoic acid (3)
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Draw the structure of but-2-enoic acid (3)
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Why are carboxylic acids with a low molecular mass very soluble in water? (1)
The -COOH group forms hydrogen bonding with water
Why are carboxylic acids considered weak acids despite being very soluble in water? (1)
They are only slightly dissociated in water
Write the dissociation equation for ethanoic acid in water. (1)
CH3COOH (aq) ⇌ CH3COO⁻ (aq) + H⁺ (aq)
What is the role of the carbonyl group in the dissociation of a carboxylic acid in water? (2)
• The carbonyl group attracts electrons away from the -OH group • Weakening the bond and allowing it to release a proton
How does the addition of a halogen atom, such as chlorine, affect the acidity of a carboxylic acid? (3)
• The halogen atom withdraws electron density away from the carbonyl carbon • Making the O-H bond more polar and easier to break. • This increases the acid’s ability to release a hydrogen ion
Draw the structure of chloroethanoic acid (2)
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How can you test for carboxylic acids using sodium carbonate? (2)
• React the carboxylic acid with sodium carbonate (Na₂CO₃) • Effervescence occurs due to the evolution of carbon dioxide gas
Write the balanced equation for the reaction of ethanoic acid with sodium carbonate. (1)
2CH₃COOH + Na₂CO₃ → 2CH₃COO⁻Na⁺ + CO₂ + H₂O
Why are ionic salts formed in the reaction between carboxylic acids and sodium carbonate? (2)
• The reaction forms carboxylate salts • Which are ionic and soluble in water.
What is the reaction called when carboxylic acids react with alcohols to form esters? (1)
Esterification
What are the products of an esterification reaction? (1)
An ester and water
What catalyst is used in the esterification reaction? (1)
Concentrated sulfuric acid (H₂SO₄)
Give the general reaction equation for esterification. (1)
RCOOH + R’OH ⇌ RCOOR’ + H₂O
Draw and label the structure of an ester functional group (2)
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What is the functional group isomer of esters?
Carboxylic acid