Make phenyl benzoate from phenol and benzoyl chloride
Use phenol and benzoyl chloride to form phenyl benzoate, applying acyl-chloride ester formation to a phenolic alcohol.
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
Which two reactants form phenyl benzoate in the syllabus example?
What you will learn
- Recall phenyl benzoate as a syllabus ester example
- Identify the phenyl and benzoate parts of its structure
- Distinguish phenol from an aliphatic alcohol
Use a phenolic alcohol
The syllabus includes phenyl benzoate as an example of ester formation from an alcohol and an acyl chloride. Phenol reacts with benzoyl chloride to form phenyl benzoate and HCl.
C₆H₅COCl + C₆H₅OH → C₆H₅COOC₆H₅ + HCl. The phenyl group from phenol is attached through oxygen to the benzoyl-derived carbonyl.
Read the ester name carefully
‘Phenyl’ identifies the group attached to the ester oxygen; ‘benzoate’ identifies the aromatic acyl portion.
Phenol is a phenolic compound, not an aliphatic alcohol, but its oxygen can form the ester under acyl-chloride conditions. Do not describe this as a simple acid-catalysed equilibrium esterification.
Pause and explain
Where is the phenyl group attached in phenyl benzoate?
Worked example
Identify the two structural parts in phenyl benzoate.
Show the worked solution
- Locate the ester oxygen.
- The phenyl group is bonded to that oxygen.
- The benzoate side contains the aromatic carbonyl group.
Answer C₆H₅COOC₆H₅ contains a benzoyl-derived benzoate portion and a phenyl group from phenol.
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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.
Write the reactants and products for phenyl benzoate formation.
Give me a hint
Use a phenolic –OH and benzoyl chloride.
Compare my reasoning
- React C₆H₅OH with C₆H₅COCl.
- Join the phenyl oxygen to the benzoyl carbonyl carbon.
- Include HCl.
C₆H₅OH + C₆H₅COCl → C₆H₅COOC₆H₅ + HCl.
Look for these in your work
- Reactants correct
- Ester structure
- HCl included
Explain the name phenyl benzoate from the product structure.
Give me a hint
Identify the group attached to oxygen and the acyl portion.
Compare my reasoning
- The phenyl group comes from phenol.
- The benzoate portion comes from benzoyl chloride.
- The ester oxygen links the two parts.
It is phenyl benzoate: phenyl is bonded through oxygen, and the carbonyl-containing acyl part is benzoate.
Look for these in your work
- Phenyl part
- Benzoate part
- Linkage described
A student names C₆H₅COOC₆H₅ ‘benzyl benzoate’. What is the structural naming error?
Give me a hint
Compare phenyl, C₆H₅–, with benzyl, C₆H₅CH₂–.
Compare my reasoning
- The oxygen is bonded directly to the phenyl ring.
- There is no CH₂ group between the ring and oxygen.
- The alcohol-derived group is phenyl, not benzyl.
The correct name is phenyl benzoate; benzyl would require an extra CH₂ group that is absent.
Look for these in your work
- Ring–O bond checked
- CH₂ checked
- Name corrected
Common mistakes
- Calling the product benzyl benzoate
- Attaching the phenyl group directly to the carbonyl carbon
- Omitting HCl
- Calling phenol an aliphatic alcohol
What can you explain now?
Which two reactants form phenyl benzoate in the syllabus example?
Compare with the explanation
Phenol and benzoyl chloride
The phenol provides the phenyl group and benzoyl chloride the acyl group.
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Make it stick
How do phenol and benzoyl chloride combine to form phenyl benzoate?
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