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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

Aus Kapitel 19:

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19.12 : Herstellung von Aminen: Alkylierung von Ammoniak und Aminen

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19.1 : Amine: Einführung

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19.2 : Nomenklatur der primären Amine

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19.3 : Nomenklatur der sekundären und tertiären Amine

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19.4 : Nomenklatur der Aryl und heterocyclischen Amine

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19.5 : Struktur der Amine

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19.6 : Physikalische Eigenschaften von Aminen

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19.7 : Basizität der aliphatischen Amine

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19.8 : Basizität der aromatischen Amine

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19.9 : Basizität von heterocyclischen aromatischen Aminen

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19.10 : NMR Spektroskopie von Aminen

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19.11 : Massenspektrometrie von Aminen

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19.13 : Herstellung von 1°-Aminen: Azid-Synthese

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19.14 : Herstellung von 1° Aminen: Gabriel-Synthese

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19.15 : Herstellung von Aminen: Reduktion von Oximen und Nitroverbindungen

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