Organic Chemistry III: Nitrogen Chemistry (Edexcel A Level Chemistry): Exam Questions

Exam code: 9CHO

31 mins3 questions
1a
2 marks

The painkiller paracetamol can be synthesised from phenol in three steps. The percentage yield for each step is shown.

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In Step 1 another product also forms. The two products can be distinguished using their 13C NMR spectra.

Complete the table to show the number of peaks in each 13C NMR spectrum.

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1b
Sme Calculator
3 marks

Calculate the minimum mass of phenol needed to synthesise 1.00 kg of paracetamol.

[Mr values: paracetamol = 151.0    phenol = 94.0]

1c
3 marks

When metabolised in the body, paracetamol forms a toxic compound Z. This is then removed in the liver by a reaction with the tripeptide glutathione.

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i) The conversion of paracetamol to compound Z is

(1)

A

addition

B

hydrolysis

C

oxidation

D

reduction

ii) Draw a circle around each of the chiral carbon atoms in glutathione.

(1)

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iii) Glutathione is formed from glycine and two other amino acids.

Which two amino acids combine with glycine to form glutathione?

(1)

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A

aspartic acid and cysteine

B

glutamic acid and cysteine

C

glutamic acid and methionine

D

aspartic acid and methionine

1d
2 marks

Explain why amino acids such as glycine are crystalline solids at room temperature.

2a
3 marks

This question is about amines.

Phenylamine is an aromatic amine and butylamine is an aliphatic amine.

Phenylamine can be prepared from nitrobenzene.

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Butylamine can be prepared from butanenitrile.

C3H7CN   →   C4H9NH2

Compare and contrast these two preparations of amines.

2b
3 marks

Compare and contrast the basicity of phenylamine and butylamine.

2c
2 marks

Write the equation for the reaction between propanoyl chloride and pentylamine.

Include the name of the amide formed. 

State symbols are not required. 

Name of amide ..................................................

2d
1 mark

A section of a polyamide is shown.

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Identify, by name or formula, the amine monomer that reacts to form this polyamide.

3a
4 marks

This question is about the amines butylamine, C4H9NH2 , and phenylamine, C6H5NH2 .    

The reaction scheme shows some reactions of butylamine, a primary amine.

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i) Write the equation for Reaction 1 to show why the pH of the solution is greater than 7. State symbols are not required.

(1)

ii)  Explain why phenylamine is a weaker base than butylamine.

(3)

3b
2 marks

Give the name and structural formula of the compound needed to react with butylamine in Reaction 2.

Name................................................................................................

Structural formula..........................................................................

3c
1 mark

What is seen when excess butylamine is used in Reaction 3?

  • blue solution

  • blue precipitate

  • yellow solution

  • yellow precipitate

3d
5 marks

i) What is the type and mechanism of the reaction in Reaction 4?

(1)

A

electrophilic addition

B

electrophilic substitution

C

nucleophilic addition

D

nucleophilic substitution

ii) Complete the diagram to show the mechanism for Reaction 4. Include curly arrows, and relevant lone pairs and dipoles.

(4)

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