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Alkylation is one of the methods used to prepare amines. Direct alkylation of ammonia or a primary amine with an alkyl halide gives polyalkylated amines along with a quaternary ammonium salt through successive SN2 reactions. This process of making the quaternary salt through the direct alkylation method is called exhaustive alkylation.

Each alkylation step makes the nitrogen center more nucleophilic, which triggers successive alkylations until a quaternary ammonium salt is formed. Considering this, specific reaction conditions, such as excess ammonia, must be used to exclusively make primary amines.

Since tertiary halides are more hindered, they are not the substrates of choice for alkylation reactions. Although secondary alkyl halides are far less hindered and can be alkylated, they are also not preferred as substrates due to their tendency to undergo elimination reactions.

Since ammonia is cheaply available, alkylations using ammonia as the substrate are the most common.

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Amine PreparationAlkylationAmmonia AlkylationAmine AlkylationSN2 ReactionQuaternary Ammonium SaltExhaustive AlkylationNucleophilicityPrimary AmineTertiary HalideSecondary Alkyl HalideElimination ReactionAmmonia Substrate

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19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

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19.1 : Amines : Introduction

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19.2 : Nomenclature des amines primaires

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19.3 : Nomenclature des amines secondaires et tertiaires

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19.4 : Nomenclature des amines aryliques et hétérocycliques

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19.5 : Structure des amines

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19.6 : Propriétés physiques des amines

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19.7 : Basicité des amines aliphatiques

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19.8 : Basicité des amines aromatiques

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19.9 : Basicité des amines aromatiques hétérocycliques

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19.10 : Spectroscopie RMN des amines

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19.11 : Spectrométrie de masse des amines

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19.13 : Préparation de 1° amines : synthèse de l’azoture

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19.14 : Préparation de 1° Amines : Synthèse de Gabriel

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19.15 : Préparation des amines : réduction des oximes et des composés nitrés

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