Acyl Chlorides (Cambridge (CIE) A Level Chemistry): Exam Questions

Exam code: 9701

46 mins5 questions
1a
1 mark

This question is about derivatives of carboxylic acids.

Fig. 1.1 shows the structure of a carboxylic acid derivative.

Displayed formula of butanoyl chloride showing the four-carbon chain with a C=O group bonded to chlorine

Fig. 1.1

State the systematic name of the carboxylic acid derivative shown in Fig. 1.1.

1b
2 marks

Ethanoyl chloride reacts with ethanol to form ethyl ethanoate as shown in Fig. 1.2.

Reaction equation showing ethanoyl chloride reacting with ethanol to form ethyl ethanoate and HCl

Fig. 1.2

i) State the name of the other product formed in this reaction.

[1]

ii) This reaction can be described as an esterification reaction or an acylation reaction.

Explain why this reaction can also be described as a condensation reaction.

[1]

1c
1 mark

Ethanoyl chloride can also react with ammonia to form ethanamide.

Construct an equation for this reaction.

1d
2 marks

During the preparation of propanoyl chloride, SO2 and HCl were also produced.

State the names of the two reactants used to form propanoyl chloride.

2a
1 mark

Propanoyl chloride is used for the synthesis of other organic compounds. 

Draw the skeletal formula for propanoyl chloride. 

2b
3 marks

i) State the names of the two products formed when propanoyl chloride undergoes hydrolysis.

[2]

ii) State the name of the mechanism by which hydrolysis occurs.

[1]

2c
2 marks

Explain why propanoyl chloride will more readily undergo hydrolysis compared to 2-chloropropane.

1a
2 marks

Acyl chlorides are commonly used carboxylic acid derivatives. 

Ethanoyl chloride reacts with an excess of ammonia. 

A student proposes the following equation to represent the reaction:

CH3COCl + NH3  →  CH3CONH2 + HCl

Correct and explain the student's error.

1b
2 marks

N-methylethanamide can also be formed from ethanoyl chloride.

i) Draw the skeletal formula of N-methylethanamide.

[1]

ii) Construct an equation for the formation of N-methylethanamide from ethanoyl chloride.

[1]

1c
1 mark

Ethanoyl chloride will react with 2-methylpropan-1-ol to form an ester.

Draw the skeletal formula of the ester formed.

2a
3 marks

This question is about butanoyl chloride.

Butanoyl chloride can be produced from butanoic acid.

i) Draw the displayed formula of butanoyl chloride.

[1]

ii) State the name and chemical formula of a reagent that converts butanoic acid into butanoyl chloride.

[2]

2b
3 marks

i) Explain why butanoic acid is a weaker acid than 2-chlorobutanoic acid.

[2]

ii) Draw the skeletal formula for 2-chlorobutanoic acid.

[1]

2c
1 mark

State the name of a chloro-substituted butanoic acid that is a stronger acid than 2-chlorobutanoic acid.

2d
4 marks

Butanoyl chloride can undergo hydrolysis.

Describe the mechanism for the hydrolysis of butanoyl chloride. Include charges, dipoles, lone pairs of electrons and curly arrows, as appropriate.

2e
5 marks

State and explain the relative ease of hydrolysis for butanoyl chloride, chlorobenzene and 1-chlorobutane.

3a
5 marks

A common method for esterification is to react an alcohol with an acyl chloride.

i) State the name of the mechanism for the reaction of butan-2-ol with ethanoyl chloride.

[1]

ii) Describe the mechanism for the reaction of butan-2-ol with ethanoyl chloride. Include charges, dipoles, lone pairs of electrons and curly arrows, as appropriate.

[4]

3b
3 marks

Acyl chlorides undergo various reactions with water, alcohols, ammonia and primary amines.

Ethanamide is the product of a chemical reaction.

State the necessary reactants and name the other product.

3c
5 marks

Ethanoyl chloride can react with primary aliphatic and aromatic amines to produce different amides.

i) Explain why ethanoyl chloride is more reactive towards ethylamine than phenylamine.

[2]

ii) Name the products of both reactions and classify the nitrogen in each product.

[3]