Syllabus Edition

First teaching 2020

Last exams 2024

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Hydroxy Compounds (A Level Only) (CIE A Level Chemistry)

Exam Questions

2 hours11 questions
1a4 marks

Phenol, C6H5OH, undergoes many different reactions.

Complete the equations in Fig. 1.1 showing all the products of each of these reactions of phenol. If no reaction occurs write no reaction in the products box.

yXlnDTOW_phenol + Na K_5JItwB_arrow  
       
yXlnDTOW_phenol + NaOH K_5JItwB_arrow  
       
yXlnDTOW_phenol + CH3CO2H K_5JItwB_arrow  
       
yXlnDTOW_phenol + Br2 (aq) K_5JItwB_arrow  

Fig. 1.1

1b1 mark

State the reaction mechanism that occurs when phenol reacts with bromine water.

1c2 marks

Phenol undergoes bromination when reacted with bromine water. Benzene also undergoes bromination but requires different reaction conditions.

State any other necessary conditions for the bromination of phenol and give the necessary reaction conditions for the bromination of benzene.

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2a2 marks

Phenol can be prepared by the reaction of phenylamine with nitric(III) acid. This reaction involves three steps.

In the first step, nitric(III) acid, HNO2, is prepared.

i)

Complete the equation to show the formation of nitric(III) acid.

_____________   +   HCl   →  HNO2   +   _____________ 

[1]

ii)
State the necessary condition for this reaction. 

[1]

2b2 marks

In the second step in the production of phenol, the diazonium salt shown in Fig. 2.1 is formed. In the final step, the diazonium salt is decomposed by warming with water to produce phenol.

7-4-2b-e-diazonium-salt

Fig. 2.1

State the formula of any other products.

2c2 marks

Phenol will react with ethanoyl chloride in the presence of sodium hydroxide and heat.

Draw the displayed formula of the organic product and state its name.

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3a1 mark

1-naphthol is a phenolic compound. Its structure is shown in Fig. 3.1.

7-4-3a-e-1-naphthol-a

Fig. 3.1

Give the molecular formula of 1-naphthol.

3b1 mark

Like phenol, 1-naphthol is a weak acid.

Write an equation to show how 1-naphthol acts as a weak acid.

3c1 mark

1-naphthol undergoes similar reactions to phenol.

Suggest the structure of the organic compound that is produced when 1-naphthol reacts with bromine water.

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1a5 marks

This question is about the reactions of the aromatic alcohol, phenol.

Phenol behaves as a weak acid.

i)
Write the equation for phenol reacting with sodium hydroxide.
[2]
ii)
Write the equation for phenol reacting with sodium metal. 
[3]

 

1b1 mark

Phenols also undergo electrophilic substitution reactions when reacted with bromine water at room temperature.

Describe two observations that can be made during this reaction.

1c2 marks

Draw the structures of the two possible products from the reaction of phenol with dilute nitric acid.

1d1 mark

Explain why 3-nitrophenol is not formed when phenol reacts with dilute nitric acid. 

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2a2 marks

This question is about phenol. 

Phenol is an aryl compound. 

i)
Give the molecular formula of phenol. 

[1]

ii)
Give the empirical formula of phenol. 

[1]

2b3 marks

Explain why phenol is a weak acid. 

You should include an equation in your answer. 

2c4 marks

Describe and explain how the acidities of ethanol and phenol compare to that of water. 

2d1 mark

Phenol reacts with bromine water. 

i)
Give the name of the product formed by this reaction.
[1]
ii)
Write a balanced chemical equation for this reaction. 
[1]

2e2 marks

Explain how the reactions of phenol and benzene with bromine can show that phenol is more reactive than benzene.  

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3a4 marks

Phenol can be prepared from phenylamine

There are three stages that take place during this preparation:

  • Stage 1: Prepare nitric(III) acid using sodium nitrate and hydrochloric acid
  • Stage 2: React phenylamine with nitric(III) acid and hydrochloric acid to form a diazonium salt 
  • Stage 3: Thermal decomposition of the diazonium salt to form phenol, hydrochloric acid, and nitrogen gas
i)
Give the essential conditions for the reaction in stage 2.
[1]
ii)
Draw the displayed formula of the diazonium salt formed in stage 2. 
[3]

3b3 marks

Write balanced symbol equations for the reactions that occur at each stage:

Stage 1: ...................................................................................................
Stage 2: ...................................................................................................
Stage 3: ...................................................................................................

3c3 marks

The diazonium salt formed during stage 2 can also react with phenol to form a useful substance, Z

i)
Give the displayed formula of Z. 
[2]
ii)
Suggest a possible use for Z
[1]
3d1 mark

The first step of substance Z involves creating the diazonium ion. 

The reaction is the same as that in stage 2 in part (a)

Explain why the reaction to produce the diazonium ion is carried out at below 10 oC. 

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4a2 marks

Rodinol is used as a photographic developer.

It can be synthesised from phenol by the following route:

rodinol-

i)
Suggest reagents and conditions for step 1. 

[1]

ii)
Name the mechanism by which this reaction occurs. 

[1]

4b3 marks
i)
What type of reaction is step II?

[1]

ii)
Give suitable reagents that could be used in step 2.

[2]

4c3 marks

Rodinol can undergo many reactions. 

Suggest the structural formulae for the compounds E, F and G in the following chart of the reaction so of rodinol. 

rodinol-reactions

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5a4 marks

Acyl chlorides are useful reagents in synthesis.

They react with aromatic compounds and also with alcohols. 

i)
Give the reagents and conditions required to make ethyl ethanoate directly from a carboxylic acid. 
[3]
ii)
Write an equation to show the formation of ethyl ethanoate in part i).
[1]

5b1 mark

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

Its structure is shown below.


7-4-5b-m-5b--phenyl-benzoate


What is the molecular formula of phenyl benzoate? 

5c3 marks
i)
Give the essential conditions needed for the reaction in part (b).

[2]
ii)
Describe one observation you would make in this reaction. 
[1]

5d3 marks

During the initial reaction to produce phenyl benzoate, the phenoxide ion is formed. 

i)
Draw the structure of this ion. 
[1]
ii)
Explain why it this ion is formed.
[1]
iii)
Write an equation for the overall reaction. 
[1]

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1a7 marks

This question is about the reactions of phenol and benzene. 

Explain the difference in bromination of phenol and benzene. In your answer, include structures of any organic products formed in the reaction. 
1b4 marks
A mixture of 2-nitrophenol and 4-nitrophenol can be formed via the pathway shown in Fig. 1.1.

4647f941-e08a-4e10-b13e-e1ffb5b28c9b

Fig. 1.1

i)
State the reagents required for reaction 1.
 
[1]
 
ii)
Calculate the mass, in grams, of phenol required to form 30 g of 2-nitrophenol assuming a 35% yield. Give your answer to three significant figures and show your working.
 
 
 
mass = ............... g
[4]
1c3 marks

Phenol reacts with sodium to form a salt and hydrogen gas in an acid-base reaction.

Explain why phenol behaves as a weak acid.

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2a4 marks

Phenyl 2-hydroxybenzoate is an antiseptic and is shown in Fig. 2.1.

7-4-2a-h-pheny-2-hydroxybenzoate-1

Fig. 2.1

A molecule of phenyl 2-hydroxybenzoate has 13 carbon atoms

i)
State the number of carbon atoms that are sp, sp2 and sp3 hybridised carbon atoms, if any, in phenyl 2-hydroxybenzoate.
 
   sp carbons ......................
 
   sp2 carbons ......................
 
   sp3 carbons ......................
 
[1]
 
ii)
Complete Table 2.1 showing the reactions of phenyl 2-hydroxybenzoate with the three reagents.
 
 Table 2.1
7-4-2a-h-pheny-2-hydroxybenzoate-2[3]

2b2 marks

Phenyl 2-hydroxybenzoate can be made from 2-hydroxybenzoic acid and phenol by heating the two compounds strongly together.

Write an equation, using the displayed formula, for this reaction.

2c3 marks

Complete and balance the equation in Fig. 2.2 for the alkaline hydrolysis of phenyl 2-hydroxybenzoate.
screenshot-2023-06-12-120213

Fig. 2.2

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3a3 marks

This question is about a drug called mesalamine (also known as 5-aminosalicylic acid) that is used to treat bowel disease. It can be synthesised from salicylic acid, the chemical structure of which is shown in Fig. 3.1

6-8_q2a-ocr-a-as--a-level-hard-sq

Fig. 3.1

State the systematic IUPAC name for salicylic acid and deduce the two positional isomers are possible, giving their names and structures.

IUPAC name of salicylic acid ............................................

positional isomer 1 positional isomer 2







 

3b2 marks

A possible two step synthesis of mesalamine is shown below in Fig. 3.2.

img-2540

Fig. 3.2

Draw the structures of compound X and mesalamine.

3c5 marks

State the reagents and conditions required for steps 1 and 2 in Fig. 3.2 in part (b).

  • step 1

   reagent(s) ...................................................

   conditions(s) .................................................

  • step 2

   reagent(s) ...................................................

   conditions(s) .................................................

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