Make ethyl ethanoate from an alcohol and an acyl chloride
React ethanol with ethanoyl chloride at room temperature to form ethyl ethanoate and HCl.
Section 33 · Carboxylic acids and derivatives
A Level; Cambridge International Chemistry 9701, 2028–2030 syllabus, Topic 33. Focus on the named compounds, reagents and conditions in each outcome; apply the specified reaction type rather than extending it to unlisted cases. Written practice is self-checked
Before you begin
- Recall carboxylic acids, esters, phenols, alcohols, halogenoalkanes and electrophilic/nucleophilic reaction ideas from earlier topics.
Work on paper. Try each question before revealing help, and explain why your method works.
Quick readiness check
What ester forms from ethanol and ethanoyl chloride?
What you will learn
- Describe ester formation from an alcohol and acyl chloride
- Use ethyl ethanoate as the syllabus example
- Identify HCl as the by-product
Build the ester linkage
An alcohol reacts with an acyl chloride to form an ester and hydrogen chloride. Ethanol plus ethanoyl chloride gives ethyl ethanoate: CH₃COCl + CH₃CH₂OH → CH₃COOCH₂CH₃ + HCl.
The alcohol supplies the ethyl group attached to the ester oxygen; the acyl chloride supplies the ethanoate part.
Use the product name to check the structure
Write the alkyl part from the alcohol first, then name the carboxylate part from the acyl chloride.
This is a nucleophilic addition–elimination reaction of an acyl chloride. The reaction is rapid at room temperature; the syllabus example focuses on ethyl ethanoate.
Pause and explain
What by-product accompanies ester formation from an acyl chloride?
Worked example
Name the ester formed from ethanol and ethanoyl chloride and write its by-product.
Show the worked solution
- Ethanol contributes ethyl.
- Ethanoyl chloride contributes ethanoate.
- The leaving chlorine and alcohol hydrogen form HCl.
Answer Ethyl ethanoate and HCl form.
Try a topic test
Choose Easy, Normal or Difficult. Save your answers and open worked review after finishing.
Test this topic →From guided practice to a new situation
Write your answer and reasoning first. Use a hint only if you are stuck. The model solution is for self-checking; your written work is not automatically marked.
Complete CH₃COCl + CH₃CH₂OH → …
Give me a hint
Join the acyl group to ethanol’s oxygen and account for H and Cl.
Compare my reasoning
- Keep the ethyl group from ethanol.
- Form the ester linkage CH₃COO–CH₂CH₃.
- Pair H and Cl as HCl.
CH₃COOCH₂CH₃ + HCl.
Look for these in your work
- Ester structure
- Ethyl group
- HCl by-product
Explain why the product name is ethyl ethanoate.
Give me a hint
Identify each reactant’s contribution.
Compare my reasoning
- Ethanol contributes ethyl.
- Ethanoyl chloride contributes the ethanoate acyl part.
- Name alkyl before carboxylate.
It is ethyl ethanoate because ethanol supplies ethyl and ethanoyl chloride supplies ethanoate.
Look for these in your work
- Alcohol part
- Acyl part
- Name order
A learner writes methyl ethanoate for this reaction. Correct the name by checking the alcohol-derived group.
Give me a hint
Count the carbons in ethanol.
Compare my reasoning
- Ethanol contains two carbons.
- The ester oxygen is attached to CH₃CH₂–.
- That group is ethyl.
The product is ethyl ethanoate, not methyl ethanoate.
Look for these in your work
- Carbon count
- Group identified
- Name corrected
Common mistakes
- Naming methyl ethanoate
- Writing ethanoic acid instead of the ester
- Forgetting HCl
- Swapping which reactant supplies the ethyl group
What can you explain now?
What ester forms from ethanol and ethanoyl chloride?
Compare with the explanation
Ethyl ethanoate
Ethanol supplies the ethyl group.
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Make it stick
Which reactants form ethyl ethanoate, and what part does each contribute?
If you needed the solution, close it and solve the problem again from a blank page. A correct answer is stronger when you can explain the reason for each step.