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ii) Ethyl alcohol, on dehydration with a strong Lewis acid, gives ethylene
(Ethanol) (Ethylene)
ii) Elimination reactions: The two groups that are eliminated are on
adjacent atoms. An atom or group from -carbon atom and a proton
from the -carbon are eliminated. In all these reactions the presence of
one hydrogen on the -carbon atom is necessary.
These -elimination reactions are also known as E2 reactions or 1,2-
elimination reactions. In such elimination reactions (i.e. E2 reactions) the
two groups being eliminated (Ex: H and X atoms) are trans to each
other. Hence E2 reactions are generally trans elimination reactions. In
such elimination reactions, the more stable trans alkene is formed as a
major product.
Ex 1: Tertiary butyl bromide, when treated with alcoholic potash, gives 2
-methyl 1-butene
Ex 2: Hofmann Elimination:
Pyrolysis of a quaternary ammonium hydroxide salts, derived from an
amine having an alkyl group that is larger than the methyl group gives
an olefin and a 30 amine. This type of elimination is known as
Hofmann elimination reaction.
OHion acts as a strong base and it abstracts the -hydrogen of the larger
alkyl group (n-propyl group in the above example) forming a -bond.
Trimethyl amine in the given example is expelled by E2 elimination. The
Hofmann elimination reaction products are generally the least substituted
alkenes. This principle is known as Hofmann rule. When two acidic -
hydrogens are present (let us call them as Ha and Hb atoms), Ha is removed
such that the least substituted alkene is predominantly formed in the
products.
In these Elimination reactions, the more stable trans alkene is the major
product.
Ex:
Ex 3: Saytzeff elimination:
In dehydrohalogenation and dehydration reactions, when two acidic -
hydrogens are present (Ha and Hb atoms), Hb is removed such that the
most substituted alkene is formed as a major product. This is known as
Saytzeff elimination rule.
(b) E2 reactions
Assignment questions: