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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.

Tags
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 of Primary Amines

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19.3 : Nomenclature of Secondary and Tertiary Amines

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19.4 : Nomenclature of Aryl and Heterocyclic Amines

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19.5 : Structure of Amines

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19.6 : Physical Properties of Amines

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19.7 : Basicity of Aliphatic Amines

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19.8 : Basicity of Aromatic Amines

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19.9 : Basicity of Heterocyclic Aromatic Amines

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19.10 : NMR Spectroscopy Of Amines

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19.11 : Mass Spectrometry of Amines

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19.13 : Preparation of 1° Amines: Azide Synthesis

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19.14 : Preparation of 1° Amines: Gabriel Synthesis

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19.15 : Preparation of Amines: Reduction of Oximes and Nitro Compounds

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