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Elimination reaction of cyclohexanol to cyclohexene with sulfuric acid and heat [1] An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. [2] The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction ...
More generally, Zaytsev's rule predicts that in an elimination reaction the most substituted product will be the most stable, and therefore the most favored. The rule makes no generalizations about the stereochemistry of the newly formed alkene, but only the regiochemistry of the elimination reaction. While effective at predicting the favored ...
An important factor in the antiperiplanar conformer is the interaction between molecular orbitals. Anti-periplanar geometry will put a bonding orbital and an anti-bonding orbital approximately parallel to each other, or syn-periplanar.
Most common is the β-elimination via the E2 or E1 mechanism. [26] A commercially significant example is the production of vinyl chloride. The E2 mechanism provides a more reliable β-elimination method than E1 for most alkene syntheses. Most E2 eliminations start with an alkyl halide or alkyl sulfonate ester (such as a tosylate or triflate).
An example of modest stereoselectivity is the dehydrohalogenation of 2-iodobutane which yields 60% trans-2-butene and 20% cis-2-butene. [5] Since alkene geometric isomers are also classified as diastereomers, this reaction would also be called diastereoselective.
The quality of stereospecificity is focused on the reactants and their stereochemistry; it is concerned with the products too, but only as they provide evidence of a difference in behavior between reactants. Of stereoisomeric reactants, each behaves in its own specific way. Stereospecificity towards enantiomers is called enantiospecificity.
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Thermolysis converts 1 to (E,E) geometric isomer 2, but 3 to (E,Z) isomer 4.. The Woodward–Hoffmann rules (or the pericyclic selection rules) [1] are a set of rules devised by Robert Burns Woodward and Roald Hoffmann to rationalize or predict certain aspects of the stereochemistry and activation energy of pericyclic reactions, an important class of reactions in organic chemistry.