Hofmann Elimination is a fundamental organic chemistry reaction that produces the least substituted alkene from an amine precursor. Named after August Wilhelm Hofmann, this reaction is notable for its deviation from Zaitsev's rule, which typically predicts the formation of the most substituted alkene. The process involves the treatment of a tertiary amine with an alkylating agent to form a quaternary ammonium salt, followed by the abstraction of a β-hydrogen using a strong base, resulting in alkene formation. Its applications are widespread in both laboratory research and industrial processes, including the synthesis of polymers and pharmaceutical intermediates.
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Hofmann Elimination is a key reaction in organic chemistry that involves the formation of the least substituted alkene from an amine precursor
Hofmann Elimination is named after the German chemist August Wilhelm Hofmann, who made significant contributions to the field of organic chemistry
Hofmann's pioneering work in organic chemistry, including his research on aniline dyes and the discovery of the Hofmann rearrangement, has had a lasting impact on the field and his legacy extends to the Royal College of Chemistry in London
Hofmann Elimination generally follows an E2 pathway and is influenced by steric effects and the nature of the base used
Hofmann Elimination is exemplified by the reaction of trimethylamine with methyl iodide to form tetramethylammonium iodide and the conversion of tert-amyl chloride to isobutene, highlighting its utility in the synthesis of alkenes from amine precursors
Hofmann Elimination is a versatile tool in organic synthesis, with applications in both academic research and industrial processes such as the production of small alkenes for polymers and pharmaceutical intermediates
Hofmann and Zaitsev Elimination are both β-elimination reactions that differ in their product selectivity, with Hofmann favoring the formation of the least substituted alkene and Zaitsev leading to the most substituted alkene
The choice of base, its steric bulk, and the reaction conditions play a significant role in determining the outcome of Hofmann and Zaitsev Elimination reactions
Hofmann Elimination involves the elimination of a β-hydrogen atom and a leaving group from an amine to form an alkene, while Hofmann Degradation involves the conversion of a primary amide to a primary amine with the loss of a carbon atom and the migration of the carbonyl group
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Hofmann Elimination precursor molecule
Tertiary amine treated with alkylating agent to form quaternary ammonium salt.
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Hofmann Elimination base requirement
Strong base needed to abstract β-hydrogen, leading to alkene and tertiary amine.
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Hofmann Elimination reaction mechanism
Follows E2 pathway, influenced by steric effects and base nature.
