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CAIE A-Level Chemistry A2 34.1 Primary and Secondary Amines Questions

Practise amine synthesis, acylation and basicity using reagents, product structures and nitrogen lone pairs.

Syllabus
2028–2030
Course
Chemistry 9701
Level
A2

Exam points

  • select halogenoalkane substitution or nitrile/amide reduction routes to a target primary or secondary amine
  • draw the N-substituted amide formed when an amine attacks an acyl chloride
  • explain basicity by proton acceptance at the nitrogen lone pair and compare alkyl electron-donating effects

Covered syllabus points

34.1.1—Preparation of primary and secondary amines34.1.2—Amide formation from amines34.1.3—Basicity of aq. solutions of amines

Question 1

[Maximum number: 2]

Phenylamine, C6H5NH2\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}, and propylamine, CH3CH2CH2NH2\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2}, can be produced by different reduction reactions.

Identify an organic compound that can be converted into CH3CH2CH2NH2\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{NH}_{2} by a reduction reaction. State the reagent for this reaction.
organic compound
reagent

Question 2

[Maximum number: 3]

Asparagine and aspartic acid are two naturally occurring amino acids. Their structures and isoelectric points are shown in Table 8.1.

Table 8.1

Table 8.1

Question (a)

(a)

Propanedioic acid, HOOCCH2COOH\mathrm{HOOCCH}_{2} \mathrm{COOH}, is treated with an excess of thionyl chloride, SOCl2\mathrm{SOCl}_{2}. Propanedioyl chloride, ClOCCH2COCl\mathrm{ClOCCH}_{2} \mathrm{COCl}, is formed.

[ 3 ]

Question (i)

(i)

Write an equation for this reaction.

[ 1 ]

Question (ii)

(ii)

Propanedioyl chloride reacts with an excess of asparagine to form compound G with molecular formula C11H16 N4O8\mathrm{C}_{11} \mathrm{H}_{16} \mathrm{~N}_{4} \mathrm{O}_{8}.

Each molecule of compound G has four amide groups.
Draw the structure of compound G.

 Compound G, C11H16 N4O8\text { Compound G, } \mathrm{C}_{11} \mathrm{H}_{16} \mathrm{~N}_{4} \mathrm{O}_{8}
[ 2 ]

Question 3

[Maximum number: 3]

Copper is a transition element and has atomic number 29.

Question (a)

(a)

Ethane-1,2-diamine is a useful reagent in organic chemistry.

[ 3 ]

Question (i)

(i)

Explain how the amino groups in ethane-1,2-diamine allow the molecule to act as a Brønsted-Lowry base.

[ 2 ]

Question (ii)

(ii)

Write an equation for the reaction of ethane-1,2-diamine with an excess of hydrochloric acid.

[ 1 ]
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