Victor Grignard discovered the Grignard reagent in 1900, for which he won the Nobel Prize in Chemistry in 1912. Grignard reagents are organometallic compounds consisting of an alkyl, vinyl or aryl group bonded to magnesium. They react productively with aldehydes, ketones, esters, epoxides, and carbon dioxide to form alcohols, acids, and ketones. Organolithium reagents, which have a more ionic carbon-lithium bond, are more reactive than Grignard reagents and react similarly with functional groups like aldehydes and ketones. Grignard and organolithium reagents are important tools for carbon-carbon bond formation in organic synthesis.
GRIGNARD REAGENT RMgX.A Grignard reagent is an organomagnesium compound which can be described by the chemical formula 'R-Mg-X' where R refers to an alkyl or aryl group and X refers to a halogen. They are generally produced by reacting an aryl halide or an alkyl halide with magnesium.A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, ..
Organolithium compounds and their preparation.pptxZaeem36
Here, the detailed explanation of organolithium compounds in this presentation you will find out about:
organolithium introduction
-Preparation
-Properties
-And their useful Reactions,
for more projects and any kind of presentations you can contact us at:
zaeem.bzn@gmail.com
GRIGNARD REAGENT RMgX.A Grignard reagent is an organomagnesium compound which can be described by the chemical formula 'R-Mg-X' where R refers to an alkyl or aryl group and X refers to a halogen. They are generally produced by reacting an aryl halide or an alkyl halide with magnesium.A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, ..
Organolithium compounds and their preparation.pptxZaeem36
Here, the detailed explanation of organolithium compounds in this presentation you will find out about:
organolithium introduction
-Preparation
-Properties
-And their useful Reactions,
for more projects and any kind of presentations you can contact us at:
zaeem.bzn@gmail.com
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The video lecture for this presentation is available at the following link on YouTube
https://youtu.be/3sxal579RNM
The presenation will be useful for Ug/PG (Chemistry) students
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The video lecture for this presentation is available at the following link on YouTube
https://youtu.be/3sxal579RNM
The presenation will be useful for Ug/PG (Chemistry) students
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Artificial Intelligence (AI) technologies such as Generative AI, Image Generators and Large Language Models have had a dramatic impact on teaching, learning and assessment over the past 18 months. The most immediate threat AI posed was to Academic Integrity with Higher Education Institutes (HEIs) focusing their efforts on combating the use of GenAI in assessment. Guidelines were developed for staff and students, policies put in place too. Innovative educators have forged paths in the use of Generative AI for teaching, learning and assessments leading to pockets of transformation springing up across HEIs, often with little or no top-down guidance, support or direction.
This Gasta posits a strategic approach to integrating AI into HEIs to prepare staff, students and the curriculum for an evolving world and workplace. We will highlight the advantages of working with these technologies beyond the realm of teaching, learning and assessment by considering prompt engineering skills, industry impact, curriculum changes, and the need for staff upskilling. In contrast, not engaging strategically with Generative AI poses risks, including falling behind peers, missed opportunities and failing to ensure our graduates remain employable. The rapid evolution of AI technologies necessitates a proactive and strategic approach if we are to remain relevant.
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2. Victor GrignardVictor Grignard
Grignard ReagentsGrignard Reagents
Grignard, Victor , 1871–1935, French chemist. He shared the
1912 Nobel Prize in Chemistry1912 Nobel Prize in Chemistry for his work in organic synthesis
based on his discovery (1900) of the Grignard Reagent. He taught
at the Univ. of Nancy (1909–19) and at the Univ. of Lyons (from
1919 until the end of his career).
3. R X + Mg R MgX
dry ether
Mg
Br
MgBr
H
I
H
MgI
Cl
MgCl
N
Cl
N
MgCl
The alkyl halides are more reactive than aryl and vinyl halides.
The reactivity of alkyl halide is RI > RBr > RCl whereas
organomagnesium fluoride are not known yet.
Solvents:
diethyl ether (b.p. 34.60
C),
diethylene glycol,
diglyme (b.p. 1600
C),
tetrahydrofuran (b.p. 660
C)
Grignard ReagentsGrignard Reagents
Halide does not contain the following functional groups –
Functional group with active hydrogen –COOH, -C≡CH, -OH, -NH2, -SH, etc
The functional group - -CO-, -CN, -NO2, -SO-, Epoxide, etc.
4.
5. Grignard Reagents - StructureGrignard Reagents - Structure
The Grignard reagent was existing in dimeric form (stabilization of Grignard
reagent) which is in equilibrium with dialkyl magnesium compound and
magnesium dihalide.
R MgX2 R2Mg + MgX2 R Mg
X
Mg R
X
The X-ray diffraction studies - R Mg
X
Mg R
X
OEt2
OEt2
OEt2
OEt2
6. Organometallic NomenclatureOrganometallic Nomenclature
C C
H
H MgBr
H
vinylmagnesium bromide
H3CH2CH2CH2C-Li
Butyllithium
(H3C)2Cu- Li+
Dimethylcopper lithium
H3C MgBr
methylmagnesium bromide
CH MgBr
H3C
H3C
H2C Mg
Br
MgBr
phenylmagnesium bromide
isopropylmagnesium bromide
benzylmagnesium bromide
C Mg
BrH2C
CH3
CH3
H
(R)-sec-butylmagnesium bromide
Organometallic compounds were normally named as substituted metals. e.g. alkyl
metal or alkyl metal halide.
7. • The difference in electronegativity between carbon and magnesium (lithium), the C-MgThe difference in electronegativity between carbon and magnesium (lithium), the C-Mg
(C-Li) bond is polar covalent, with C(C-Li) bond is polar covalent, with Cδδ--
and Mgand Mgδδ++
((LiLiδδ++
))
– Grignard and organolithium reagents behave like carbanions/nucleophile
• CarbanionCarbanion: an anion in which carbon has an unshared pair of electrons and bears a: an anion in which carbon has an unshared pair of electrons and bears a
negative charge.negative charge.
Grignard and Organolithium Reagents – ReactivityGrignard and Organolithium Reagents – Reactivity
• The carbon-lithium bond in CH3Li has about 40% ionic character, and the carbon-
magnesium bond in CH3MgCl has about 35% ionic character. Therefore organolothium
are more reactive than Girgnard reagent.
8. phenylmagnesium bromide
MgBr
Br
Mg/dry ether
H + MgBr(OH)
H2O
ROH
H + MgBr(OR)
O2
OOMgBr OOH
HCl
OH
D2
O
D + MgBr(OD)
RCOOH
H + MgBr(OOCR)
Reactivity of Grignard reagent
with active hydrogen
Grignard Reagents – ReactivityGrignard Reagents – Reactivity
9. phenylLithium
Li
H
Li/dry ether
H + LiOH
H2O
ROH
H + LiOR
O2
OOLi OOH
HCl
OH
D2
O
D + LiOD
RCOOH
H + RCOOLi
Reactivity of organolithium
reagent with active hydrogen
RNH2
H + RNHLi
Organolithium Reagents – ReactivityOrganolithium Reagents – Reactivity
10. formaldehydeformaldehyde to give primary alcoholsto give primary alcohols
aldehydesaldehydes to give secondary alcoholsto give secondary alcohols
ketonesketones to give tertiary alcoholsto give tertiary alcohols
estersesters to give tertiary alcoholsto give tertiary alcohols
COCO22 to give acidsto give acids
epoxides to give primary alcoholsto give primary alcohols
cyanidecyanide to ketone or acidto ketone or acid
Grignard reagents react productively with:Grignard reagents react productively with: