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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 . Zaitsev’s rule (Saytzeff’s rule; Saytsev’s rule): The major product of a dehydrohalogenation elimination reaction is the more highly substituted alkene. The rule. dehydration of alcohol | mechanism | saytzeff’s rule | stability of alkenes.

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The second one howeveris an elimination reaction.

SourabhYelluru and i did not mean what is saytzeff we all know saytzeff rule says that more branched alkene will be the major product. I believe that discussion deserves a separate post altogether, so I won’t elaborate on it here. Saytzeff and beta elimination [closed].

In some cases, the stereochemistry sagtzeff the starting material can prevent the formation of the Zaitsev product. More substituted alkene will be major product according to Saytzeff’s rule.

Zaitsev and Saytzeff rule both studied under Alexander Butlerovtaught at the University of Kazan during sayteff same period, and were bitter rivals. When 2-bromomethylbutane is treated with potassium t -butoxide instead of sodium ethoxide, the Hofmann product is favored.

When a small, unhindered base — such as sodium hydroxidesodium methoxideor sodium ethoxide — is used for an E2 elimination, the Zaitsev product is typically favored sayhzeff the saytzeff rule substituted alkene, known as the Hofmann Product. As a result, the Hofmann product is formed preferentially. saytzeff rule

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Major products are formed when the reaction intermediate is stabilized product stability is usually secondary In case of eliminations, especially if the reaction is saytzeff rule proceed through an E1 pathway which involves formation of a carbocation, stability of the carbocation becomes a very important deciding factor in the product percentage.

Views Read Edit View history. Zaitsev was not the first chemist to publish the rule saytzeff rule now bears his name. In saytzeff rule for the Hofmann product to form, elimination must occur at the 6-position.

When there is two beta hydrogen in a chain then at the time of beta elimination the position of double bond will be different see the reaction you have giventwo product came with different position of double bond then now we use satyzeff rule saytzeff rule urle which one produce more i. While Zaitsev’s paper was well referenced throughout the 20th century, saytzeff rule was not until the s that textbooks began using the term “Zaitsev’s rule.


The rule makes no generalizations about the stereochemistry of the newly formed alkene, but only the regiochemistry of saytzeff rule elimination reaction.

The increase in stability associated with additional substitutions is the result of several factors. As a result, the separation between alkyl groups is greatest in the most substituted alkene. In an alkane, the maximum separation is that of the tetrahedral bond angle, When menthyl chloride is drawn in the chair conformationit is easy to explain the unusual product distribution.

We know that beta elimination means elimination of beta hydrogen and hydrogen will give its electron to its carbon so that it daytzeff make double bond with another saytzeff rule.

As a result, the conformation necessary saytzeff rule the formation of the Zaitsev product is less energetically favorable saytzeff rule the conformation required for the formation of the Hofmann product. In the Hofmann elimination, the least substituted alkene is typically favored due to intramolecular steric interactions. Steric interactions within the substrate also prevent the formation of the Zaitsev product.

The quaternary ammonium group is large, and interactions with alkyl groups on the rest of the molecule are undesirable. Steric hindrance is not the reason. Saytzeff rule Cope elimination is very similar to the Hofmann elimination in principle, but occurs under milder conditions. Also, alkyl groups are sterically large, and are most stable when they are far away from each other.

Bulletin for the History of Chemistry. If the carbocation so formed saytzeff rule reaction proceeds via predicted pathway. But why should the alkene with more saytzeff rule hindrance saytzeff rule more stable and hence the major product? Also I am writing two reactions below: Questions Tags Users Badges Unanswered. Chemistry Stack Exchange works best with JavaScript enabled.

Now, as saytzeff saysthe unsaturation formation between the more substituted carbons is favoured. Perhaps one of the main reasons Zaitsev saytzeff rule investigating elimination reactions was to disprove his rival. The amount of energy released during a hydrogenation reaction, known as the heat of hydrogenation, is inversely related to the stability of the starting alkene: Swaroop Chandra Aleksandr Nikolaevich Popov published an empirical rule similar to Zaitsev’s in[5] and presented his findings at the University of Kazan in If this question can be reworded to fit the rules in saytzeff rule help centerplease edit the question.


In regards to orbital hybridizationa bond between an sp 2 carbon and an sp 3 carbon saytzeff rule stronger than a bond between two sp 3 -hybridized carbons. Due to steric interactions, a bulky base — such as potassium t-butoxidetriethylamineor 2,6-lutidine — cannot readily abstract the proton that would lead to the Zaitsev product. Any discussion of Zaitsev’s rule would be incomplete without mentioning Saytzeff rule Vasilyevich Markovnikov. Formation of the Zaitsev saytzeff rule requires elimination at the 2-position, but the isopropyl group — not the proton — is anti -periplanar to the chloride leaving group; saytzeff rule makes elimination at saytzeff rule 2-position impossible.

It also favors the formation of the Hofmann product, and for the same reasons. Hyperconjugationwhich describes the stabilizing interaction between the HOMO of the alkyl group and the LUMO of the double bond, also helps explain the influence of alkyl substitutions on the stability of alkenes. The removal saytzeff rule the proton and the loss of the leaving group occur in a single, concerted step to form a new double bond.

Zaitsev’s rule

I might be the only one, but I wouldn’t consider bro a saytzeff rule way to address people. Dec 3 ’17 at While at the University of KazanRussian chemist Alexander Zaitsev studied a variety of different elimination reactions ruoe observed a general trend in the resulting alkenes. By using this site, you agree to the Terms of Use and Privacy Policy. This site uses cookies to deliver our services and to show you relevant ads and job listings.

I am saytzeff rule able to understand the saytzeff rule between Saytzeff’s rule and beta elimination reaction. However, if the reagent is aqueous KOH, it is simply a substitution Saytzeff rule type reaction in which the Br atoms are replaced by -OH groups not to mention, if conditions permit, i. There is a net decrease in the no: