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Concept
Elimination reaction
Summary
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. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism.
The E2 mechanism, where E2 stands for bimolecular elimination, involves a one-step mechanism in which carbon-hydrogen and carbon-halogen bonds break to form a double bond (C=C Pi bond).
The specifics of the reaction are as follows:
E2 is a single step elimination, with a single transition state.
It is typically undergone by primary substituted alkyl halides, but is possible with some secondary alkyl halides and other compounds.
The reaction rate is second order, because it's influenced by both the alkyl halide and the base (bimolecular).
Because the E2 mechanism results in the formation of a pi bond, the two leaving groups (often a hydrogen and a halogen) need to be antiperiplanar. An antiperiplanar transition state has staggered conformation with lower energy than a synperiplanar transition state which is in eclipsed conformation with higher energy. The reaction mechanism involving staggered conformation is more favorable for E2 reactions (unlike E1 reactions).
E2 typically uses a strong base. It must be strong enough to remove a weakly acidic hydrogen.
In order for the pi bond to be created, the hybridization of carbons needs to be lowered from sp3 to sp2.
The C-H bond is weakened in the rate determining step and therefore a primary deuterium isotope effect much larger than 1 (commonly 2-6) is observed.
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In organic chemistry, a substituent is one or a group of atoms that replaces (one or more) atoms, thereby becoming a moiety in the resultant (new) molecule. (in organic chemistry and biochemistry, the terms substituent and functional group, as well as side chain and pendant group, are used almost interchangeably to describe those branches from the parent structure, though certain distinctions are made in polymer chemistry. In polymers, side chains extend from the backbone structure.
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