E2 MECHANISM AND

EXAMPLES
BY
-TEJASWINI B.V
 ELIMINATION REACTION
• 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. 
 E2 REACTION
• E2 is one of four major reaction mechanisms you'll 
encounter early in your study of organic chemistry. 
The E stands for elimination. Two atoms on adjacent 
carbons are removed, or eliminated, in order to obtain 
the product. The end result is an alkene with a new C-C 
pi bond. The 2 in the mechanism name stands for 
bimolecular. This means that the rate of the reaction 
depends on the concentration of the substrate, the 
organic molecule undergoing elimination, as well as the 
base that is required for the reaction.
 EXAMPLES OF E2 REACTIONS

• All E2 reactions have two things in common: a good leaving 
group and a hydrogen atom on a carbon adjacent to the one 
with the leaving group. Alkyl halides and alcohols are the 
most common reactants in an E2 reaction. Here are some 
examples of E2 reactions.
• Alkyl halides undergo elimination to produce alkenes.
• Alcohols undergo elimination to produce alkenes.
• Notice that E2 elimination of an alcohol uses acid, not base. 
As we'll see when we look at the mechanism, the acid is 
used to make the -OH group into a better leaving group, 
which is wate
 E2 MECHANISM
•The general form of the E2 mechanism is as follows:

    
     B: = base
X = leaving group (usually halide or tosylate)
•In the E2 mechanism, a base abstracts a proton neighboring the leaving 
group, forcing the electrons down to make a double bond, and, in so 
doing, forcing off the leaving group. When numerous things happen 
simultaneously in a mechanism, such as the E2 reaction, it is called a 
concerted step.
An example of this type of reaction in scheme 1 is the reaction of 
isobutylbromide with potassiumethoxide in ethanol. The reaction 
products are isobutylene, ethanol and potassium bromide.
An example of the E2 reaction

Base Strength: A strong base is required since the base is involved 
in the rate-determining step.
Leaving groups: A good leaving group is required, such as a halide 
or a tosylate, since it is involved in the rate-determining step.
Stereochemistry requirements: Must occur with antiperiplanar 
stereochemistry.
•
TO SUM UP....!
The reaction 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.
• E2 competes with the SN2 reaction mechanism if the base can also act as a nucleophile (true
for many common bases).
THANKYOU!