Title: Hofmann rule
Long Title: IUPAC Gold Book - Hofmann rule
DOI: 10.1351/goldbook.H02830
Status: current

Definition
"The principal olefin formed in the decomposition of quaternary ammonium hydroxides that contain different primary alkyl groups is always ethylene, if an ethyl group is present." Originally given in this limited form by A. W. Hofmann, the rule has since been extended and modified as follows: "When two or more alkenes can be produced in a $\upbeta\!$-elimination reaction, the alkene having the smallest number of alkyl groups attached to the double bond carbon atoms will be the predominant product." This orientation described by the Hofmann rule is observed in elimination reactions of quaternary ammonium salts and tertiary sulfonium salts, and in certain other cases.

Related Terms
- Zaitsev rule: https://goldbook.iupac.org//terms/view/S05481
- alkenes: https://goldbook.iupac.org//terms/view/A00224
- alkyl groups: https://goldbook.iupac.org//terms/view/A00228
- decomposition: https://goldbook.iupac.org//terms/view/D01547
- elimination: https://goldbook.iupac.org//terms/view/E02038

Source
- PAC, 1994, 66, 1077. 'Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)' on page 1121 (https://doi.org/10.1351/pac199466051077)

Other Outputs
- html: https://goldbook.iupac.org/terms/view/H02830/html
- json: https://goldbook.iupac.org/terms/view/H02830/json
- xml: https://goldbook.iupac.org/terms/view/H02830/xml

Citation: Citation: 'Hofmann rule' in IUPAC Compendium of Chemical Terminology, 5th ed. International Union of Pure and Applied Chemistry; 2025. Online version 5.0.0, 2025. 10.1351/goldbook.H02830
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Accessed: 2026-05-27T22:50:14+00:00