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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Comment section

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

  1. 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.

  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. 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.

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