Hofmann elimination of alkylammonium salts to give alkenes

by James

Description: Tetra-alkyl ammonium salts undergo elimination to form the least substituted alkene. This is called the Hofman elimination.
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{ 6 comments… read them below or add one }

Ned Silavwe March 10, 2012 at 5:26 am

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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james March 13, 2012 at 9:10 am

Thanks for the spot! Fixed.

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Stanton de Riel January 16, 2013 at 11:51 am

That’s one f in Hofmann ….

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james January 17, 2013 at 12:06 pm

Thank you.

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Karthik May 20, 2015 at 2:08 pm

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?

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James May 20, 2015 at 11:51 pm

Probably nothing would happen. You might get a little bit of methanol and NMe3 via substitution (SN2).

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