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Master Organic Chemistry Reaction Guide

Hofmann elimination of alkylammonium salts to give alkenes

Description: Tetra-alkyl ammonium salts undergo elimination to form the least substituted alkene. This is called the Hofman elimination.

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Real-Life Example:
Org. Synth. 1969, 49, 39
DOI Link: 10.15227/orgsyn.049.0039

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9 thoughts on “Hofmann elimination of alkylammonium salts to give alkenes

  1. Hey James; love the content thus far. I believe the Newman projection on the left may be missing a carbon from the main alkyl chain (4 shown when there should be 5). I don’t know if that was intentional, but regardless I just want to say thanks for making this website.
    Much love.

  2. Just curious. What would happen if we tried reacting Tetramethyl Ammonium with a mild base (like AgOH). Since there is no beta Hydrogen to abstract, Hofmann elimination isn’t feasible so what would be the products?

  3. I appreciate your well presented information. I just wanted to ask whether you meant, under bonds broken, C1-H and not C2-H. That is in the first (i.e, general) equation. Later on, under mechanism, the information looks correct.
    Thank you.

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