Preparations of alkene

1. From Alkyne : By partial

hydrogenation

Na / liq. NH

3

C trans-cy clooctene
(CH2)6 .
C
Lindlars cataly st

cis-cy clooctene

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 2. From alkyl Halide : : dehydrohalogenation heating with alcoholic potash (potassium
hydroxide dissolved in alcohol,say, ethanol i.e.,removal of halogen acid. This is example
of β-elimination reaction, since hydrogen atom is eliminated from the β carbon atom

Nature of halogen atom and the alkyl group determine rate of the reaction. It is observed that for
halogens, the rate is: iodine > bromine > chlorine, while for alkyl groups it is : tert > secondary >
primary.

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Why is anti elimination preferred?
The elimination occurs from a staggered conformation which is lower in energy than an eclipsed
conformation needed for syn elimination. In this manner the steric interaction between the base and the
leaving group are also minimized.

The base abstracts a hydrogen on an ADJACENT carbon to leaving group in a single step

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Saytzeff’s Rule:

Hoffmann’s product.

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Regioselectivity-The tendency of a reaction to preferentially produce one constitutional isomer.
Stereoselectivity-The tendency of a reaction to produce one of two stereoisomers in unequal amounts.
Stereospecificity-Used to describe a reaction in which the configuration of the product is dependent on the
configuration of the starting material.

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36.

(b) From vicinal dihalides: Dihalides in

which two halogen atoms are attached to
two adjacent carbon atoms are known as
vicinal dihalides. Vicinal dihalides on
treatment with zinc metal lose a molecule
of ZnX2 to form an alkene. This reaction
is known as dehalogenation.

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From alcohols by acidic dehydration:
group takes out one hydrogen atom from the
β-carbon atom.

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