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Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.

Under thermal conditions, the hydroxide can abstract a proton from the β carbon; this generates an alkene with the simultaneous release of a neutral amine molecule. This elimination process is called the Hofmann elimination. For the elimination to occur, the β proton and tertiary amine group must be positioned opposite or anti-periplanar to each other. This reaction yields the less substituted alkene as the major product, also known as the Hofmann product.

Tags
Hofmann EliminationAminesAlkenesE2 EliminationQuaternary Ammonium SaltAlkyl HalideHydroxide SaltcarbonAnti periplanarHofmann ProductLess Substituted Alkene

Aus Kapitel 19:

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19.21 : Amine zu Alkenen: Hofmann-Eliminierung

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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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19.12 : Herstellung von Aminen: Alkylierung von Ammoniak und 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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