Question
The azide anion is a nucleophile and when attached to a carbon atom, undergoes reduction to the amino group and free nitrogen. Suggest a method of preparation of the primary amine propanamine.
Step 1
Start with propyl bromide (1-bromopropane) as the starting material. This compound has a carbon-bromine bond that can be easily replaced by the azide anion. Show more…
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The cyanide anion is a nucleophile and when attached to a carbon atom, is reduced to a primary amine. Suggest a method of preparing propanamine from chloroethane.
Primary amines can also be prepared by the reaction of an alkyl halide with azide ion, followed by catalytic hydrogenation. What advantage do this method and the Gabriel synthesis have over the synthesis of a primary amine using an alkyl halide and ammonia?
Preparation of primary amines using azide ion avoids the problem of over-alkylation since the alkyl azide is not nucleophilic. The alkyl azide is prepared from an alkyl halide via an SN2 reaction with N3 as the nucleophile. Subsequent reduction of the azide with LiAlH4 leads to the desired amine. Draw curved arrows to show the movement of electrons in this step of the mechanism.
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