Organometallic

Compounds
Contents
Introduction Reactivity Applications

1 3 5

2 4 6

Properties Reactions Environmental Concerns

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 What are
1 Organometallic
Compounds?
“Organometallic Compounds are
chemical compounds which
contain at least one bond between
a metallic element and a carbon
atom belonging to an organic
”
molecule.
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 Introduction
Organometallic compounds are normally named as substituted
metals, for example, alkyl metal.
The bond between the metal atom and the carbon belonging to
the organic compound is usually covalent in nature. When metals
like sodium, with relatively high electro positivity, form these
compounds, a carbanionic nature is shown by the carbon which is
bound to the central metal atom.

An example of an organometallic compound wherein carbons belonging to a benzene

molecule bond with chromium is displayed above.

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 Properties of Organometallic Compounds
 The bond between carbon atom and the metal is usually highly covalent in
nature.
 Most of the organometallic compounds exist in solid states, especially the
compounds in which the hydrocarbon groups have a ring structure or they are
aromatic.
 The compounds consisting of highly electropositive metals, like sodium, are
very volatile and can undergo spontaneous combustion.

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 Especially the compounds that are volatile in nature, organometallic compounds
are found to be toxic to humans.
 These compounds can act as reducing agents, especially the compounds formed
by highly electropositive metals.
From the points listed above, it can be observed that the properties of metals that
constitute the organometallic compounds, make the organometallic compounds
different from each other.

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 Reactivity

methyl chloride methyllithium methylmagnesium bromide

CH3Cl CH3Li CH3MgBr

The images show the electrostatic potentials for methyl chloride, methyl
lithium and methyl magnesium bromide. 
The redder an area is, higher is the electron density and bluer an area is,
lower is the electron density.

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Reactivity
l
e thy sity l y ,
e m
d e n
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e, on le the ctron le bro
a lid lectr ophi , m m.
l h r e tr iu m e le hi s iu ss h i u
y e c p e
e alk low  ele y
h
l lit ighe cleo
r
agn is le yl lit
s n m p t h
th
In up ha d is
a
m eth as h a nu t
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hy l gro at m
e
n I n p h i s e y
gro e) a rou ) and
m
In meth rich
th
1 l u g d
(b 2 (re the tron
c
3 ele

So, organometallic compounds react as anionic carbon or electron rich atoms, which means they
will function as either bases or nucleophiles.

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Reactions
Organometallic compounds go through several important reactions, some are
named below:

 Asociative and dissociative substitution
 Oxidative addition and reductive elimination
 Electron transfer
 Carbon-hydrogen bond activation
 Cyclometalation
 Nucleophilic Substitution and Addition

We will look at some in the next slide…

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Reactions
In principle there are 3 important groups of reactions where nucleophiles attack electrophilic C atoms.
For the organometallic reagents these types of reactions will result in the formation of new C-C bonds.

General Mechanism Organometallic Application

1. Nucleophilic Substitution:

R2CuLi with alkyl halides or

tosylates to give alkanes

2. Nucleophilic Addition:

RLi or RMgX with aldehydes or

ketones to give 2o or 3o alcohols

3. Nucleophilic Acyl Substitution:

RLi or RMgX with esters to
give 3o alcohols

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Applications
In various commercial chemical
reactions, organometallic
compounds are used as
homogeneous catalysts.
These compounds are used in
bulk hydrogenation processes
like the manufacture of
margarine.
These compounds are used as
stoichiometric reagents in
research-oriented chemical and
industrial reactions.
These compounds are used as
reagents during the synthesis
of some organic compounds,
and they can also behave as
catalysts.
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More Applications
The complexes formed
from compounds like
these are useful in the
facilitation of the
production of many
organic compounds.
These compounds are also
used in the manufacture of
various semiconductors, which
require the use of compounds,
like trimethylgallium.
They are also used in the
production of LEDs or light
emitting diodes.
The points above discuss the
importance of such compounds.
However, they are also the
cause of many environmental
concerns. Let’s look at them
now…
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 “Environmental Concerns”

Contaminant and natural organometallic compounds are

present in the environment. Some are waste of human use,
such as organomercury compounds and organolead.
Organometallic compounds were also largely used in anti-
fouling paints but have been banned now because of
environmental concerns. The organometallic
compound, roxarsone is a controversial animal feed
additive and is shown above.
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References
.
www.wikipedia.com
www.britanicca.com
www.byjus.com Place your screenshot here

www.sciencedirect.com
www.masterorganicchemistry.com

This presentation is designed and completed by

Hanzala Labeeb, CMS : 333860, CHE-13 B.

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