Elimination reaction, is a class of organic
chemical reactions that involves the
removal of a pair or group of atoms from a
molecule, generally through the
movement of acids, bases, or metals and
in few cases, by means of heating to a
high temperature. It is the main process
with the aid of which natural/organic
compounds containing saturated
compounds are transformed to
unsaturated compounds.
Mechanisms of Elimination Reaction:
An elimination reaction is a type of organic
reaction in which two substituents are removed
from a molecule in either 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
number 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).
Characteristics of E1 Mechanism
1. Unimolecular (depends on concentration of
substrate)
2. 3°>2°>1° (formation of carbocation)
3. Two-step process of elimination:
a. Ionization: the carbon-halogen bond breaks to give a
formation of carbocation.
b. Deprotonation of the carbocation.
4. Reactions occurs in the complete absence or the
presence of only a week base.
5. In competition with SN1 because they share a
common carbocationic intermediate.
6. Highly polar ionizing
7. Follows Zaitsev’s Rule (the most substituted alkene
is usually the major product)
8. Method of Elimination: Dehydrohalogenation and
Dehalogenation
9. Examples:
Characteristics of E2 Mechanism
1. Bimolecular (depends on concentration of substrate
and base)
2. Single step elimination, with a single transition state
(the double bond begins to form and the H and X groups
are leaving)
3. It requires strong base. It must be strong enough to
remove a weakly acidic hydrogen.
4. Competes with SN2 mechanism if the base can also act
as a nucleophile which are true with common bases.
5. Solvent polarity not important.
6. Follows Hoffman Elimination (the least substituted
alkene that is predominantly product in which the leaving
group is quartenary amine)
7. Involves Cope Elimination (involving an amine oxide)
8. Method of Elimination: dehydrohalogenation,
dehalogenation, dehydration, and dehydrogenation
9. Examples:
9. Examples:
Elimination reactions are commonly known by the kind
of atoms or group of atoms leaving the molecule. The
following are the methods of elimination reaction and
their important products and preparations: