Organic Synthesis Insight

Virtual Textbook of Organic Synthesis

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Saytzeff Rule

Saytzeff Rule implies that base-induced eliminations (E2) will lead predominantly to the olefin in which the double bond is more highly substituted, i.e. that the product distribution will be controlled by thermodynamics. The use of sterically hindered bases raises the activation energy barrier for the pathway to the product predicted by Saytzeff's Rule. Thus, a sterically hindered base will preferentially react with the least hindered protons, and the product distribution will be controlled by kinetics.


Double bond formation due to loss of water molecule It is an elimination reaction. According to Saytzeff's rule , during dehydration, more substituted alkene (olefin) is formed as a major product.

Greater the substitution of double bond greater is the stability of Alkene

When the more substituted alkene is the major product of dehyrohalogenation the reaction is said to follow Zaitsev rule ( Saytzeff, Saytseff, or Saytzev ). The major product is referred to as Zaitsev product. If the major product is the less substituted alkene the reaction is following Hoffmann rule and the product is Hoffmann product.

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named/concepts/saytzeff_s_rule.txt · Last modified: 2017/02/14 00:51 by webadmin

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