Alcohols (Cambridge (CIE) A Level Chemistry): Exam Questions

Exam code: 9701

27 mins3 questions
1a
4 marks

Acyl chlorides and carboxylic acids can both be used to synthesise esters.

i) State the reagents and conditions required to make ethyl ethanoate directly from a carboxylic acid.

[3]

ii) Construct an equation to show the formation of ethyl ethanoate in part i).

[1]

1b
1 mark

Phenyl benzoate is made from the reaction between benzoyl chloride and phenol.

Its structure is shown below.

Structural formula of phenyl benzoate showing two benzene rings connected by an ester linkage

Deduce the molecular formula of phenyl benzoate.

1c
3 marks

i) State the reagents and conditions needed for the reaction in part (b).

[2]

ii) State one observation you would make in this reaction.

[1]

1d
3 marks

During the standard synthesis of phenyl benzoate, phenol is first converted into the phenoxide ion.

i) Draw the skeletal formula of the phenoxide ion.

[1]

ii) Explain why phenol is converted into the phenoxide ion before the addition of benzoyl chloride.

[1]

iii) Construct an equation for the overall reaction between the phenoxide ion and benzoyl chloride.

[1]

2a
1 mark

An ester is prepared by reacting propan-2-ol, (CH3)2CHOH, with ethanoyl chloride, CH3COCl.

Construct an equation for this reaction.

2b
4 marks

Describe the mechanism for the reaction in part (a).

Include all relevant curly arrows, lone pairs, and dipoles.

2c
2 marks

Aldehydes can be prepared from acyl chlorides. A sample of an aldehyde is suspected to be contaminated with unreacted CH3COCl.

i) State the name of a reagent that could be used to test for the presence of CH3COCl in the sample.

[1]

ii) State the observation for a positive test.

[1]

3a
2 marks

Phenol reacts with ethanoyl chloride to form a new product.

i) Draw the skeletal formula of the organic product formed in this reaction.

[1]

ii) State the systematic (IUPAC) name of this organic product.

[1]

3b
4 marks

Describe the mechanism for the reaction occurring in part (a).

Include all relevant curly arrows, lone pairs, and dipoles.

3c
3 marks

Explain why phenol acts as a weak acid.