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-
eliminationreactions
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
Cite as:
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.
https://doi.org/10.1351/goldbook.
