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

Exam Questions

31 mins3 questions
1a2 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
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3 marks

Calculate the minimum mass of phenol needed to synthesise 1.00 kg of paracetamol.
[Mr values: paracetamol = 151.0    phenol = 94.0]

1c3 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
1d2 marks

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

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2a3 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.

2b3 marks

Compare and contrast the basicity of phenylamine and butylamine.

2c2 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 ..................................................

2d1 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.

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3a4 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)

3b2 marks

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

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

Structural formula..........................................................................
3c1 mark

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

  A blue solution
  B blue precipitate
  C yellow solution
  D yellow precipitate

3d5 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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