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Alkylation

Alkylation

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Amit Dobariya
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49 views3 pages

Alkylation

Alkylation

Uploaded by

Amit Dobariya
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Alkylation is the shifting of an alkyl group from one molecule to another.

The alkyl
group can be shifted in various forms like carbanion, cabene, free radical or
carbocation, depending on the situation and reaction.

Alkylation is a chemical process through which an alkyl group is attached to some


organic substrate molecule by methods like addition and substitution. The Alkyl
group is an alkane that lacks one hydrogen atom. A methyl group is the simplest
alkyl group consisting of one carbon atom and three hydrogen atoms. Alkylation
occurs in the presence of strong mineral acid or lewis acid, such as metal oxides,
by using electrophilic alkylating agents like olefin and alkyl halide. In the case of
aromatic compounds, alkylation leads to the addition of some simple carbon chains
to the benzene ring. There is a contrasting process to alkylation known as
dealkylation, which involves the removal of the alkyl group from a compound.
There are several types of alkylating agents, and there are several uses of alkylation
not just in organic chemistry but also in the field of biology.

Types of Alkylating Agents

● Nucleophilic alkylating agents :

Nucleophilic alkylating agents form a species called carbanion. These


alkylating agents displace halide substitutes on the given carbon atom via
an SN2 mechanism. One of the most common examples of a reaction
involving nucleophilic alkylating agents is “Suzuki coupling”, which involves
displacement of a halide group from the compound. Examples of
nucleophilic alkylating agents are grignard reagents and some more
organometallic compounds.

● Alkylation by electrophilic alkylating agents :

Electrophilic alkylating agents produce carbocation, which is also


equivalent to an alkyl cation. This alkylating agent group includes alkyl
halides like trimethyloxonium and tetrafluoroborate due to their overt
positive charge and inert leaving group. The catalysts used for this
alkylation are lewis acid and bronsted acid. Lewis acids like aluminium
trichloride. Lewis acids are usually used when alkyl halides are being used.
Bronsted acids are used in case alkylation is being done with olefins. Some
most common catalysts are zeolites.

There are several hazards of using electrophilic alkylating agents because


this type of alkylating agent is toxic and carcinogenic and tends to alkylate
the DNA. Consequently, the DNA gets coiling problems because alkylated
DNA does not coil or uncoil properly, or it cannot be processed by the
specific enzymes used to decode information. The most widely used
alkylation reaction is Friedel Crafts Alkylation reaction.

Friedel Crafts Alkylation Reaction

This reaction involves adding an alkyl group to benzene via an electrophilic


aromatic substitution reaction—for example, the addition of a methyl group
to benzene. A pi bond attacks a carbocation from an aromatic ring in this
reaction. Thus the carbocation acts like an electrophile in Friedel-crafts
alkylation.

Uses

Uses of Alkylation in Biology

One of the most common types of alkylation , methylation, is affected by vitamin


B-12 and radical-SAM-based enzymes in nature. Methylation is a chemical
reaction involving shifting a methyl group to some organic compound. It can be
done via addition reaction or substitution reaction, and there are two types of
methylation: chemical methylation and biological methylation. Other biological
uses of alkylation are: it is used for the treatment of breast cancer, germ-cell
testicular cancer, ovarian cancer and lung cancer, to name a few.

Uses of Alkylation in Daily Use Products


There are several daily use products like feedstock and detergents. For instance,
sodium dodecylbenzene is obtained by the alkylation of benzene with dodecane.

Uses of Alkylation in Gasoline

Alkylation plays a significant role in oil refinery operations by alkylating


isobutane. Some alkenes have a lesser molecular weight in the presence of
bronsted acid and zeolite as a catalyst. Alkylate is also an essential part of avgas.

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