International A LevelChemistryEdexcelExam Questions5: Transition Metals and Organic Nitrogen Chemistry5.5 Organic Chemistry: Nitrogen Compounds

Organic Chemistry: Nitrogen Compounds (Edexcel International A Level Chemistry)

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5.5 Organic Chemistry: Nitrogen Compounds

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5.5 Organic Chemistry: Nitrogen Compounds

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1a1 mark

Chlorpheniramine is an amine used in the treatment of hayfever.

q11-paper-5-jan-2022-edexcel-ial-chemistry

Deduce the classification of the labelled amine group.

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1b4 marks

The compound pyridine is used in the synthesis of chlorpheniramine.

3d-w4~dl_q11b-paper-5-jan-2022-edexcel-ial-chemistry

Like many amines, pyridine is miscible with water and the solution formed is alkaline.

Explain each of these properties of pyridine.

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1c4 marks

A student suggested that the final step in the synthesis of chlorpheniramine starts with the reaction between monodesmethylchlorpheniramine and chloromethane.

Assuming the reaction is similar to that between ammonia and chloromethane, complete the mechanism for this proposed reaction.
Some of the organic structures shown have been simplified.

Include curly arrows, and any relevant dipoles and lone pairs of electrons.

q11c-paper-5-jan-2022-edexcel-ial-chemistry

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2a2 marks

This question is about polymers.

The diagram shows part of the structure of a polymer formed by a condensation reaction between two amino acids.
q12a-paper-5-jan-2022-edexcel-ial-chemistry
Predict the structures of the two monomers that produce this polymer.

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2b2 marks

The diagram shows a repeat unit of an addition polymer used in some food wraps. It is formed from two different monomers.
q12b-paper-5-jan-2022-edexcel-ial-chemistryDeduce the structures of the two monomers that produce this polymer.

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2c
Sme Calculator2 marks

A synthetic rubber polymer has the structure shown.

q12c-paper-5-jan-2022-edexcel-ial-chemistry
The molar mass of the synthetic rubber is approximately 300 000 g mol−1.

Calculate the approximate number of repeat units in the polymer.

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3a
Sme Calculator5 marks

This question is about the investigation of an organic compound X.
X is a liquid at room temperature and pressure, which turns damp red litmus paper blue.

i)
Name the functional group present in X.

(1)

ii)
When 0.493 g of X was vaporised, 157 cm3 of dry air was displaced, measured at 15 °C and 103 000 Pa.

Calculate the molar mass of X, using the ideal gas equation.
You must show your working.

(4)

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3b
Sme Calculator5 marks

X reacted vigorously with ethanoyl chloride forming steamy fumes and a white solid Y.

i)
Identify the steamy fumes, by name or formula.
(1)

ii)
Suggest the functional group present in Y.
(1)

iii)
Analysis of Y showed that its composition by mass was 62.6% carbon; 11.3% hydrogen; 12.2% nitrogen; 13.9% oxygen.

Determine the empirical formula of Y. You must show your working.
(3)

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3c6 marks

A simplified high resolution proton NMR spectrum of Y is shown.
The relative peak areas are given near each peak.

q19c-paper-5-june-2021-edexcel-ial-chemistry

Deduce the structure of Y, using the NMR spectrum and the other information in the question.

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3d1 mark

Draw the structure of compound X.

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1a1 mark

Organic molecules are an important source of colour both in the natural world and in a wide range of industrial applications.

Curcumin contributes to the yellow colour of turmeric spice and is used as an additive in cosmetics and foods. It has been suggested that curcumin can act as an antioxidant and anticancer agent, through reactions with free radicals and proteins, and may also inhibit Alzheimer’s disease by complexing to toxic metal ions.

q21-1-paper-5-oct-2021-edexcel-ial-chemistry

Azo dyes are synthetic compounds that do not occur naturally. They can be used to colour textiles such as cotton. The acid‐base indicator methyl red is an azo dye.

q21-2-paper-5-oct-2021-edexcel-ial-chemistry

Indigotin is used to dye denim a blue colour and coumarin 440 is used to generate blue light in lasers. Both dyes occur naturally in plants but can be synthesised in the laboratory.

q21-3-paper-5-oct-2021-edexcel-ial-chemistry

The equation shows the reaction between a free radical T• and curcumin (shown by a simplified structure).

q21a-paper-5-oct-2021-edexcel-ial-chemistry

Complete the left‐hand side of the equation by adding curly half‐arrows.

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1b3 marks

Selenide anions attached to protein side‐chains may undergo nucleophilic addition reactions with curcumin.

Complete the mechanism for one of the steps in such a reaction, adding curly arrows to the simplified structures shown.

q21b-paper-5-oct-2021-edexcel-ial-chemistry

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1c2 marks

Curcumin anions can act as bidentate ligands in metal‐curcumin (M‐curc) complexes. The oxygen atoms of the curc ligand occupy adjacent coordination sites in the complex, as shown.

q21c-paper-5-oct-2021-edexcel-ial-chemistry

Complete the table relating to two M‐curc complexes.

 

[Au(curc)2]+

 [Al(curc)(C2H5OH)2(NO3)2]
Coordination number 4  
O–M–O bond angle 90°  
Shape   octahedral
Charge on metal ion   +3

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1d7 marks

An incomplete synthesis for methyl red starting from 2‐nitrobenzaldehyde and phenylamine is shown.

q21d-paper-5-oct-2021-edexcel-ial-chemistry
i)
State the reagents and conditions needed in Step X.

(2)

ii)
Draw the structure of compound A.

(1)

iii)
State the reagents needed in Step Y.

(1)

iv)
Draw the structure of compound B.

(1)

v)

The temperature used in Steps Y and Z should be kept as close to 5 °C as possible. State why the temperature should be neither higher nor lower than 5 °C.

(2)

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1e
Sme Calculator5 marks

Indigotin can be synthesised from 2‐nitrobenzaldehyde and propanone in aqueous sodium hydroxide.

q21e-paper-5-oct-2021-edexcel-ial-chemistry
i)
Complete the equation for this reaction.
q21e-i-paper-5-oct-2021-edexcel-ial-chemistry

(2)

ii)
Calculate the mass of 2‐nitrobenzaldehyde required to make 10.0 g of indigotin from this reaction when the percentage yield is 85.0%.

(3)

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1f3 marks

Give the structure of the organic product of each of the following reactions of coumarin 440.

q21f-paper-5-oct-2021-edexcel-ial-chemistry
i)
Hydrolysis with excess aqueous sodium hydroxide.

(2)

ii)
Condensation with ethanoyl chloride.

(1)

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