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Reactions of Amines as Nucleophiles

When ammonia in an ethanol solvent reacts with a halogenoalkane a primary amine is produced by the nucleophilic substitution of the halide by an NH2 group. However, the primary amine produced is also a nucleophile and in turn reacts with the halogenoalkane to form a secondary amine.The secondary amine reacts to form a tertiary amine and the tertiary amine reacts to form a quaternary ammonium salt.The nucleophilic substitution reaction of ammonia and a halogenoalkane is not a very efficient way of preparing an amine because of the further substitutions. The ammonia in a large excess will give a better yield of the primary amine.

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Specification: OCR Chemistry A (H432), A-level, 6.2.1 Amines. Topic: Nitrogen Compounds.

Key terms in this lesson

nucleophile
An atom or group of atoms that can donate a pair of electrons to form a new covalent bond.
nucleophilic substitution
A reaction mechanism in which a nucleophile donates a lone pair of electrons to an electron-deficient carbon atom, displacing a leaving group.

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