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Lab 3: grignard reaction

Objective

The purpose of this laboratory exercise is to perform a classic method for the synthesis of secondary alcohols: the addition of a Grignard reagent to an aldehyde (other than formaldehyde).

Background information

After the most remarkable discovery by Victor Grignard in 1900, organometallic (An organic compound containing a metal atom directly attached to a carbon) compounds are very useful in organic synthesis. This discovery changed the course of organic chemistry and earned him the Nobel Prize in 1912. We now refer to such compounds as Grignard Reagents.

The Grignard reaction is one of the characteristic reactions of carbonyl compounds. It is especially useful as a means of forming new carbon-carbon bonds, something that we haven't seen much of until now. In this type of reaction a C-M bond is present (C=carbon and M=metal) which is covalent in nature. The metal is usually magnesium but lithiummore reactive and is also used. The more polar the C-M bond is, the more will be its reactivity. The reactivity order is known from electrochemical series:

M= Li>K>Ca>Na>Mg>Al>Zn>Fe>Sn etc

Traditionally alkyl magnesium halides are known as Grignard reagent (R-Mg-X).

All kinds of alkyl halides react (Iodides are more reactive than bromides which in turn are more reactive than chlorides) and amazingly, even bromobenzene and other aryl bromides and iodides react easily with magnesium. This is particularly surprising since the aromatic halogen is so unreactive. For example, it is inert to refluxing with aqueous sodium hydroxide at temperatures in excess of 200˚C. The unshared pair of electrons on ether oxygen complexing with the Mg is believed to contribute to the stability of the reagent. Note: Aryl halides (ArX) and vinyl halides that are inert to nucleophilic substitution are reactive with this Grignard reaction.

Preparation and mechanism of grignard reagent:

The mechanism of Grignard reagent (GR) is not clear till today, but it is believed that the reaction is taking place on the metal surface. Since GR does not react with aprotic solvents (e.g. ether, THF etc), these solvents are widely used. The mechanism of formation of GR as follows: it goes via one electron transfer, followed by rapid combination of organic group with the metal center. From the mechanistic point of view, carbon-bromine bond should be broken prior to the reaction with magnesium.

Solutions of some Grignard reagents such as methylmagnesium bromide, ethylmagnesium bromide, and phenylmagnesiumbromides are commercially available. Here is an example of Grignard reaction which explains the effect of solvent.

The Grignard reagent is made from the direct reaction of magnesium with an alkyl halide.

The key to the function of the Grignard reagent is the reversal of the normal polarity of bonds to carbon (This type of reversal of polarity in carbon center is known as Umpolung). Because magnesium is more electropositive than carbon the carbon acquires a δ size 12{δ - {}} {} charge whereas carbon, when it has a charge at all, usually has δ + size 12{δ+{}} {} charge from bonding to halogens, oxygen, and nitrogen.

Questions & Answers

what is the stm
Brian Reply
is there industrial application of fullrenes. What is the method to prepare fullrene on large scale.?
Rafiq
industrial application...? mmm I think on the medical side as drug carrier, but you should go deeper on your research, I may be wrong
Damian
How we are making nano material?
LITNING Reply
what is a peer
LITNING Reply
What is meant by 'nano scale'?
LITNING Reply
What is STMs full form?
LITNING
scanning tunneling microscope
Sahil
how nano science is used for hydrophobicity
Santosh
Do u think that Graphene and Fullrene fiber can be used to make Air Plane body structure the lightest and strongest. Rafiq
Rafiq
what is differents between GO and RGO?
Mahi
what is simplest way to understand the applications of nano robots used to detect the cancer affected cell of human body.? How this robot is carried to required site of body cell.? what will be the carrier material and how can be detected that correct delivery of drug is done Rafiq
Rafiq
what is Nano technology ?
Bob Reply
write examples of Nano molecule?
Bob
The nanotechnology is as new science, to scale nanometric
brayan
nanotechnology is the study, desing, synthesis, manipulation and application of materials and functional systems through control of matter at nanoscale
Damian
Is there any normative that regulates the use of silver nanoparticles?
Damian Reply
what king of growth are you checking .?
Renato
What fields keep nano created devices from performing or assimulating ? Magnetic fields ? Are do they assimilate ?
Stoney Reply
why we need to study biomolecules, molecular biology in nanotechnology?
Adin Reply
?
Kyle
yes I'm doing my masters in nanotechnology, we are being studying all these domains as well..
Adin
why?
Adin
what school?
Kyle
biomolecules are e building blocks of every organics and inorganic materials.
Joe
anyone know any internet site where one can find nanotechnology papers?
Damian Reply
research.net
kanaga
sciencedirect big data base
Ernesto
Introduction about quantum dots in nanotechnology
Praveena Reply
what does nano mean?
Anassong Reply
nano basically means 10^(-9). nanometer is a unit to measure length.
Bharti
do you think it's worthwhile in the long term to study the effects and possibilities of nanotechnology on viral treatment?
Damian Reply
absolutely yes
Daniel
how to know photocatalytic properties of tio2 nanoparticles...what to do now
Akash Reply
it is a goid question and i want to know the answer as well
Maciej
characteristics of micro business
Abigail
for teaching engĺish at school how nano technology help us
Anassong
How can I make nanorobot?
Lily
Do somebody tell me a best nano engineering book for beginners?
s. Reply
there is no specific books for beginners but there is book called principle of nanotechnology
NANO
how can I make nanorobot?
Lily
what is fullerene does it is used to make bukky balls
Devang Reply
are you nano engineer ?
s.
fullerene is a bucky ball aka Carbon 60 molecule. It was name by the architect Fuller. He design the geodesic dome. it resembles a soccer ball.
Tarell
what is the actual application of fullerenes nowadays?
Damian
That is a great question Damian. best way to answer that question is to Google it. there are hundreds of applications for buck minister fullerenes, from medical to aerospace. you can also find plenty of research papers that will give you great detail on the potential applications of fullerenes.
Tarell
how did you get the value of 2000N.What calculations are needed to arrive at it
Smarajit Reply
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Source:  OpenStax, Chem217labsfall07. OpenStax CNX. Oct 16, 2007 Download for free at http://cnx.org/content/col10463/1.4
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