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Saytzeff rule

Synonym: Zaitsev rule

Dehydrohalogenation of secondary- and tertiary-alkyl halides proceeds by the preferential removal of the β-hydrogen from the carbon that has the smallest number of hydrogens. Originally formulated by A. Saytzeff (Zaitsev) to generalize the orientation in β-elimination reactions of alkyl halides, this rule has been extended and modified, as follows: When two or more olefins can be produced in an elimination reaction, the thermodynamically most stable alkene will predominate. Exceptions to the Saytzeff rule are exemplified by the Hofmann rule.
Source:
PAC, 1994, 66, 1077 (Glossary of terms used in physical organic chemistry (IUPAC Recommendations 1994)) on page 1162
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IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). XML on-line corrected version: http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. doi:10.1351/goldbook.
Last update: 2014-02-24; version: 2.3.3.
DOI of this term: doi:10.1351/goldbook.S05481.
Original PDF version: http://www.iupac.org/goldbook/S05481.pdf. The PDF version is out of date and is provided for reference purposes only. For some entries, the PDF version may be unavailable.
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