Carboxylic acids can react with alcohols to form esters in a process called esterification. Pentyl methanoate is an ester that has a distinctive fruity smell. Describe how pentyl methanoate could be identified as an ester, and explain the conditions needed to produce it from its parent carboxylic acid and alcohol. Name the two reactants used.
Written & reviewed by James Millett — Biology (Imperial College London), PGCE Science (University of Cambridge).
Model answer (5 marks)
Pentyl methanoate is an ester because it contains the ester functional group –COO–.
It can be identified as an ester by:
1. The presence of a carbonyl carbon bonded to an –O– group (C=O and C–O–C).
2. A characteristic fruity smell, typical of esters.
3. Infrared absorption at ~1735 cm⁻¹ (C=O stretch) and a weaker band at ~1250 cm⁻¹ (C–O stretch).
To produce it from its parent carboxylic acid and alcohol:
1. React methanoic acid (formic acid) with pentan‑1‑ol (pentanol).
2. Use a strong acid catalyst, e.g. concentrated H₂SO₄, to protonate the carbonyl oxygen.
3. Heat the mixture under reflux to drive off water and shift the equilibrium toward ester formation.
The two reactants are methanoic acid and pentan‑1‑ol.
It can be identified as an ester by:
1. The presence of a carbonyl carbon bonded to an –O– group (C=O and C–O–C).
2. A characteristic fruity smell, typical of esters.
3. Infrared absorption at ~1735 cm⁻¹ (C=O stretch) and a weaker band at ~1250 cm⁻¹ (C–O stretch).
To produce it from its parent carboxylic acid and alcohol:
1. React methanoic acid (formic acid) with pentan‑1‑ol (pentanol).
2. Use a strong acid catalyst, e.g. concentrated H₂SO₄, to protonate the carbonyl oxygen.
3. Heat the mixture under reflux to drive off water and shift the equilibrium toward ester formation.
The two reactants are methanoic acid and pentan‑1‑ol.
Examiner tips
- Use the term ‘ester functional group –COO–’ to secure the identification mark.
- Mention both the characteristic smell and IR bands to show understanding of ester properties.
- State the acid catalyst and reflux explicitly – these are the key conditions.
- Name the reactants correctly (methanoic acid and pentan‑1‑ol).
Common mistakes
- Calling the acid ‘formic acid’ without specifying it as methanoic acid.
- Omitting the acid catalyst or the need for reflux.
- Using the wrong alcohol name (e.g. pentanol instead of pentan‑1‑ol).
Mark scheme (5 marks)
- Pentyl methanoate is an ester because it contains the ester functional group / linkage (-COO-) OR esters are formed from a carboxylic acid and an alcohol
- Named reactant 1: methanoic acid (the parent carboxylic acid)
- Named reactant 2: pentan-1-ol / pentanol (the parent alcohol)
- An acid catalyst is needed (concentrated sulfuric acid)
- Heat / reflux is required for the reaction to occur
Key terms in this question
esterification · ester · carboxylic acid · alcohol
Related
- All WJEC A-Level Chemistry (Wales) revision notes →
- How to answer a "Describe" question →
- Decode the mark scheme abbreviations →
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