CAIE A Level Chemistry 34.1.1 Primary & Secondary Amines

Practise choosing substitution or reduction routes to primary and secondary amines with correct conditions, comparing halogenoalkanes, nitriles and amides as starting materials.

Exam points

heat a halogenoalkane with NH3 in ethanol under pressure to form a primary amine
heat a halogenoalkane with a primary amine in ethanol in a sealed tube to form a secondary amine
reduce a nitrile with LiAlH4 or H2/Ni, or an amide with LiAlH4, while preserving its carbon skeleton

[Maximum number: 2]

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

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

M1: propylamide / propenamide / $\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CONH}_{2} \mathrm{OR}$ propanenitrile / $\mathrm{C}_{2} \mathrm{H}_{5} \mathrm{CN}$

M2: $\mathrm{LiAlH}_{4}$

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34.1.1—Preparation of primary and secondary amines question 1